Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids

ABSTRACT

The present invention relates to novel combined laundry detergent, bleach, and antimicrobial composition incorporating novel sulfoperoxycarboxylic acid compounds, and methods for making and using them. The sulfoperoxycarboxylic compounds used in compositions of the invention are storage stable, water soluble and have low to no odor. Compositions of the invention may be in the form of a liquid, a solid, or a gel. The sulfoperoxycarboxylic compounds useful in preparing compositions of the present invention can be formed from non-petroleum based renewable materials.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation in part of U.S. patent applicationSer. No. 12/413,189, filed on Mar. 27, 2009. U.S. patent applicationSer. No. 12/413,189 claims priority to U.S. Provisional Application Ser.No. 61/040,444, filed on Mar. 28, 2008 and entitled“SULFOPEROXYCARBOXYLIC ACIDS, THEIR PREPARATION AND METHODS OF USE ASBLEACHING AND ANTIMICROBIAL AGENTS.” The entire contents of theseearlier-filed patent applications are hereby expressly incorporatedherein by reference including, without limitation, each of thespecification, claims, and abstract, as well as any figures, tables, ordrawings thereof.

FIELD OF THE INVENTION

The present invention relates to detergents, e.g., laundry detergents,incorporating sulfoperoxycarboxylic acid compounds.

BACKGROUND

Peroxycarboxylic acids are known for use as antimicrobials (inhibition,sanitizing, disinfecting, and sterilizing) and bleaching agents.However, conventional peroxycarboxylic acids have inherent disadvantagesof limited storage stability and water solubility. Further, mostperoxycarboxylic acids have an unpleasant odor. Thus, a need exists forstorage stable, low or no odor, water soluble peroxycarboxylic acidcompounds and compositions that also possess cleaning and detergency,antimicrobial (inhibition, sanitizing, disinfecting, and sterilizing)and bleaching properties.

SUMMARY

In some aspects, the present invention relates to novelsulfoperoxycarboxylic acids, and methods for making them. The compoundsof the invention are storage stable, have low or no-odor, and are watersoluble. Further, the compounds of the present invention can be derivedfrom non-petroleum based, renewable oils.

In some aspects, the present invention provides methods for using thecompounds of the present invention as detergents, bleaching and/orantimicrobial agents. In some aspects, the present invention providesmethods for using the compounds of the invention as antimicrobial agentsthat can inhibit or sanitize or disinfect or sterilize woven ornon-woven textile fabrics. In some aspects, the present inventionprovides methods for using the compounds of the invention as couplingagents. In some aspects, the present invention provides methods forusing the compounds of the present invention as woven or non-woventextile laundering detergents. In yet some other aspects, the presentinvention provides methods for low foaming bleach hydrotropes anddetergents for laundering woven or non-woven textile fabrics incommercially available wash systems used in the consumer or industrialor institutional market places; including, but not limited to,continuous or batch: tunnel washers, washer extractors, textile-presoakwash systems, and for top or side loading washing machines. In yet someadditional aspects, the present invention provides for using compoundsof the present invention for multi-utility wash machines that canpresoak, wash, extract, dry, or any combination thereof.

In some embodiments, the compounds and compositions of the presentinvention are suitable for use as low temperature bleaches, e.g., atabout 40 degrees Celsius. In some embodiments, the compounds of thepresent invention are suitable for use as pH optimized peroxygenbleaches, in combination with alkaline detergents. In some embodiments,the present invention includes a method for using the compounds andcompositions of the present invention as color safe, textile tolerantbleaches for textiles, e.g., wools and cotton.

In some embodiments, the novel sulfoperoxycarboxylic acids are providedin a composition including about 0.05 wt % to about 50 wt % of the novelsulfoperoxycarboxylic acid compound; about 0.1 wt % to about 75 wt % ofan oxidizing agent; about 0.1 wt % to about 40 wt % of a C₁-C₂₂carboxylic acid in combination with one C₁ to C₂₂ peroxycarboxylic acid;about 0.50 wt % to about 70 wt % of a surfactant; about 0.0 wt % toabout 5 wt % of an acid; and about 0.0 to about 10 wt % of a viscosityreducer.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graphical depiction of the stability profile ofperoxyoctanoic acid over time when contacted with different testsolutions.

FIG. 2 is a graphical depiction of the stability of an exemplarycomposition of the present invention over time at an elevatedtemperature.

FIG. 3 is a graphical depiction of the ability of selected compositionsof the present invention to stabilize percarboxylic acids over time.

FIG. 4 is a graphical depiction of the bleaching performance ofcompositions of the present invention compared to commercially availablebleaching agents.

FIG. 5 is a graphical depiction of the stability profile ofperoxyoctanoic acid in combination with exemplary compositions of thepresent invention.

FIG. 6 is a graphical depiction of the coupling capabilities of aselected composition of the present invention.

FIG. 7 is a graphical depiction of the stability of selected sulfonatedperacids in aqueous solutions over time.

FIG. 8 is a graphical depiction of the bleaching abilities of selectedsulfonated peracids compared to peroxyacetic acid.

FIG. 9 graphically depicts the efficacy of selected sulfonated peracidsagainst Staphylococcus aureus at ambient temperature.

FIG. 10 graphically depicts the efficacy of selected sulfonated peracidsagainst Escherichia coli at ambient temperature.

DETAILED DESCRIPTION

The present invention relates to sulfoperoxycarboxylic acids of FormulaI, and methods of making and using them. In some embodiments, thesulfoperoxycarboxylic acids of the invention are not sulfonated at theterminal position of the carboxylic acid chain. Unlike conventionalperoxycarboxylic acids, it has been found that the sulfoperoxycarboxylicacids of the present invention are low-odor, water soluble, and storagestable. The compounds of the present invention can be used as a puresolid powder, or blended with additional functional ingredients, forexample, chelators, buffers, or other cleaning agents. They can also beincorporated into liquid, solid, or gel formulas. The compounds andcompositions of the present invention have many uses including, but notlimited to, detergents, antimicrobials, bleaches, and coupling agents.

So that the invention maybe more readily understood, certain terms arefirst defined.

As used herein, “weight percent,” “wt-%,” “percent by weight,” “% byweight,” and variations thereof refer to the concentration of asubstance as the weight of that substance divided by the total weight ofthe composition and multiplied by 100. It is understood that, as usedhere, “percent,” “%,” and the like are intended to be synonymous with“weight percent,” “wt-%,” etc.

As used herein, the term “about” refers to variation in the numericalquantity that can occur, for example, through typical measuring andliquid handling procedures used for making concentrates or use solutionsin the real world; through inadvertent error in these procedures;through differences in the manufacture, source, or purity of theingredients used to make the compositions or carry out the methods; andthe like. The term “about” also encompasses amounts that differ due todifferent equilibrium conditions or different reaction levels for acomposition resulting from a particular initial mixture. Whether or notmodified by the term “about”, the claims include equivalents to thequantities.

It should be noted that, as used in this specification and the appendedclaims, the singular forms “a,” “an,” and “the” include plural referentsunless the content clearly dictates otherwise. Thus, for example,reference to a composition containing “a compound” includes acomposition having two or more compounds. It should also be noted thatthe term “or” is generally employed in its sense including “and/or”unless the content clearly dictates otherwise.

As used herein, the phrases “objectionable odor,” “offensive odor,” or“malodor,” refer to a sharp, pungent, or acrid odor or atmosphericenvironment from which a typical person withdraws if they are able to.Hedonic tone provides a measure of the degree to which an odor ispleasant or unpleasant. An “objectionable odor,” “offensive odor,” or“malodor” has an hedonic tone rating it as unpleasant as or moreunpleasant than a solution of 5 wt-% acetic acid, propionic acid,butyric acid, or mixtures thereof.

As used herein, the term “microorganism” refers to any noncellular orunicellular (including colonial) organism. Microorganisms include allprokaryotes. Microorganisms include bacteria (including cyanobacteria),spores, lichens, fungi, protozoa, virinos, viroids, viruses, phages, andsome algae. As used herein, the term “microbe” is synonymous withmicroorganism.

As used herein, the phrase “food product” includes any food substancethat might require treatment with an antimicrobial agent or compositionand that is edible with or without further preparation. Food productsinclude meat (e.g. red meat and pork), seafood, poultry, produce (e.g.,fruits and vegetables), eggs, living eggs, egg products, ready to eatfood, wheat, seeds, roots, tubers, leafs, stems, corns, flowers,sprouts, seasonings, or a combination thereof. The term “produce” refersto food products such as fruits and vegetables and plants orplant-derived materials that are typically sold uncooked and, often,unpackaged, and that can sometimes be eaten raw.

As used herein, the phrase “plant” or “plant product” includes any plantsubstance or plant-derived substance. Plant products include, but arenot limited to, seeds, nuts, nut meats, cut flowers, plants or cropsgrown or stored in a greenhouse, house plants, and the like. Plantproducts include many animal feeds.

As used herein, the phrase “meat product” refers to all forms of animalflesh, including the carcass, muscle, fat, organs, skin, bones and bodyfluids and like components that form the animal. Animal flesh includes,but is not limited to, the flesh of mammals, birds, fishes, reptiles,amphibians, snails, clams, crustaceans, other edible species such aslobster, crab, etc., or other forms of seafood. The forms of animalflesh include, for example, the whole or part of animal flesh, alone orin combination with other ingredients. Typical forms include, forexample, processed meats such as cured meats, sectioned and formedproducts, minced products, finely chopped products, ground meat andproducts including ground meat, whole products, and the like.

As used herein the term “poultry” refers to all forms of any bird kept,harvested, or domesticated for meat or eggs, and including chicken,turkey, ostrich, game hen, squab, guinea fowl, pheasant, quail, duck,goose, emu, or the like and the eggs of these birds. Poultry includeswhole, sectioned, processed, cooked or raw poultry, and encompasses allforms of poultry flesh, by-products, and side products. The flesh ofpoultry includes muscle, fat, organs, skin, bones and body fluids andlike components that form the animal. Forms of animal flesh include, forexample, the whole or part of animal flesh, alone or in combination withother ingredients. Typical forms include, for example, processed poultrymeat, such as cured poultry meat, sectioned and formed products, mincedproducts, finely chopped products and whole products.

As used herein, the phrase “poultry debris” refers to any debris,residue, material, dirt, offal, poultry part, poultry waste, poultryviscera, poultry organ, fragments or combinations of such materials, andthe like removed from a poultry carcass or portion during processing andthat enters a waste stream.

As used herein, the phrase “food processing surface” refers to a surfaceof a tool, a machine, equipment, a structure, a building, or the likethat is employed as part of a food processing, preparation, or storageactivity. Examples of food processing surfaces include surfaces of foodprocessing or preparation equipment (e.g., slicing, canning, ortransport equipment, including flumes), of food processing wares (e.g.,utensils, dishware, wash ware, and bar glasses), and of floors, walls,or fixtures of structures in which food processing occurs. Foodprocessing surfaces are found and employed in food anti-spoilage aircirculation systems, aseptic packaging sanitizing, food refrigerationand cooler cleaners and sanitizers, ware washing sanitizing, blanchercleaning and sanitizing, food packaging materials, cutting boardadditives, third-sink sanitizing, beverage chillers and warmers, meatchilling or scalding waters, autodish sanitizers, sanitizing gels,cooling towers, food processing antimicrobial garment sprays, andnon-to-low-aqueous food preparation lubricants, oils, and rinseadditives.

As used herein, the term “ware” refers to items such as eating andcooking utensils, dishes, and other hard surfaces such as showers,sinks, toilets, bathtubs, countertops, windows, mirrors, transportationvehicles, and floors. As used herein, the term “warewashing” refers towashing, cleaning, or rinsing ware. Ware also refers to items made ofplastic. Types of plastics that can be cleaned with the compositionsaccording to the invention include but are not limited to, those thatinclude polycarbonate polymers (PC), acrilonitrile-butadiene-styrenepolymers (ABS), and polysulfone polymers (PS). Another exemplary plasticthat can be cleaned using the compounds and compositions of theinvention include polyethylene terephthalate (PET).

As used herein, the phrase “air streams” includes food anti-spoilage aircirculation systems. Air streams also include air streams typicallyencountered in hospital, surgical, infirmity, birthing, mortuary, andclinical diagnosis rooms.

As used herein, the term “waters” includes food process or transportwaters. Food process or transport waters include produce transportwaters (e.g., as found in flumes, pipe transports, cutters, slicers,blanchers, retort systems, washers, and the like), belt sprays for foodtransport lines, boot and hand-wash dip-pans, third-sink rinse waters,and the like. Waters also include domestic and recreational waters suchas pools, spas, recreational flumes and water slides, fountains, and thelike.

As used herein, the phrase “health care surface” refers to a surface ofan instrument, a device, a cart, a cage, furniture, a structure, abuilding, or the like that is employed as part of a health careactivity. Examples of health care surfaces include surfaces of medicalor dental instruments, of medical or dental devices, of electronicapparatus employed for monitoring patient health, and of floors, walls,or fixtures of structures in which health care occurs. Health caresurfaces are found in hospital, surgical, infirmity, birthing, mortuary,and clinical diagnosis rooms. These surfaces can be those typified as“hard surfaces” (such as walls, floors, bed-pans, etc.,), or fabricsurfaces, e.g., knit, woven, and non-woven surfaces (such as surgicalgarments, draperies, bed linens, bandages, etc.,), or patient-careequipment (such as respirators, diagnostic equipment, shunts, bodyscopes, wheel chairs, beds, etc.,), or surgical and diagnosticequipment. Health care surfaces include articles and surfaces employedin animal health care.

As used herein, the term “instrument” refers to the various medical ordental instruments or devices that can benefit from cleaning with acomposition according to the present invention.

As used herein, the phrases “medical instrument,” “dental instrument,”“medical device,” “dental device,” “medical equipment,” or “dentalequipment” refer to instruments, devices, tools, appliances, apparatus,and equipment used in medicine or dentistry. Such instruments, devices,and equipment can be cold sterilized, soaked or washed and then heatsterilized, or otherwise benefit from cleaning in a composition of thepresent invention. These various instruments, devices and equipmentinclude, but are not limited to: diagnostic instruments, trays, pans,holders, racks, forceps, scissors, shears, saws (e.g. bone saws andtheir blades), hemostats, knives, chisels, rongeurs, files, nippers,drills, drill bits, rasps, burrs, spreaders, breakers, elevators,clamps, needle holders, carriers, clips, hooks, gouges, curettes,retractors, straightener, punches, extractors, scoops, keratomes,spatulas, expressors, trocars, dilators, cages, glassware, tubing,catheters, cannulas, plugs, stents, scopes (e.g., endoscopes,stethoscopes, and arthroscopes) and related equipment, and the like, orcombinations thereof.

As used herein, “agricultural” or “veterinary” objects or surfacesinclude animal feeds, animal watering stations and enclosures, animalquarters, animal veterinarian clinics (e.g. surgical or treatmentareas), animal surgical areas, and the like.

As used herein, a “laundry machine” refers to any device for launderingwoven or non-woven textile fabrics in commercially available orexperimental wash systems used in the consumer and/or industrial and/orinstitutional markets; including, but not limited to, continuous washers(e.g., tunnel type continuous batch washers), batch washer extractors,textile-presoak wash systems, steam systems, dry-wash devices and otherdry cleaning devices, and/or top or side loading washing machines (e.g.,those used in the residential or small institutional markets). Thisincludes laundering systems that are multi-utility wash machines, e.g.,those that can presoak, wash, extract, steam, dry, or any combinationthereof. A typical laundry facility may consist of multiple singlewashing machines or continuous load washers (e.g., tunnel washers), or acombination thereof.

As used herein, a “textile” is any woven or non-woven fabric or article,or garment including, but not limited to, all types found in theconsumer, industrial, and/or institutional markets including, but notlimited to, those made of cotton, poly-cotton blends, wool, aramids,polyurethanes, olefins, polyactids, nylons, silk, hemp, rayon, flax,jute, acrylics, polyesters, those made from many other synthetic ornatural fibers and mixtures thereof.

As used herein, the term “phosphorus-free” or “substantiallyphosphorus-free” refers to a composition, mixture, or ingredient thatdoes not contain phosphorus or a phosphorus-containing compound or towhich phosphorus or a phosphorus-containing compound has not been added.Should phosphorus or a phosphorus-containing compound be present throughcontamination of a phosphorus-free composition, mixture, or ingredients,the amount of phosphorus shall be less than 0.5 wt %. More preferably,the amount of phosphorus is less than 0.1 wt %, and most preferably theamount of phosphorus is less than 0.01 wt %.

For the purpose of this patent application, successful microbialreduction is achieved when the microbial populations are reduced by atleast about 50%, or by significantly more than is achieved by a washwith water. Larger reductions in microbial population provide greaterlevels of protection.

As used herein, the term “caustic free” or “alkali caustic free” or“substantially caustic” or “substantially alkali caustic free” refers toa composition, mixture, or ingredient that does not contain significantresidual and titrate-able carbonate alkalinity from alkali metalhydroxides such as sodium hydroxide or potassium hydroxide, or does notcontain an alkali metal hydroxide-containing compound or to which alkalimetal hydroxide-containing compound has not been added. The pH of suchcompositions or mixtures may be below a pH of about 9.0, below a pH ofabout 8.0 or below a pH of about 7.0. Should an alkali metalhydroxide-containing compound be present through contamination of analkali metal hydroxide-free composition, mixture, or ingredients, theamount of alkali metal hydroxide or caustic component shall be less thanabout 0.5 wt %, or less than about 0.2 wt %.

In some embodiments, an alkali metal hydroxide may be used in thecomposition, mixture, or ingredients for neutralization, stabilization,or pH adjustment purposes. If an alkali metal hydroxide is included forsuch a purpose, the amount of alkali metal hydroxide or causticcomponent shall be less than about 10.0 wt %, than about 5.0 wt %, orthan about 2.0 wt %.

As used herein, the terms “chelating agent” and “sequestrant” refer to acompound that forms a complex (soluble or not) with water hardness ions(from the wash water, soil and substrates being washed) in a specificmolar ratio. Chelating agents that can form a water soluble complexinclude sodium tripolyphosphate, ethylenediaminetetraacetic acid (EDTA),diethylene triamine pentaacetic acid (DTPA), nitrilotriacetic acid(NTA), citrate, and the like. Sequestrants that can form an insolublecomplex include sodium triphosphate, zeolite A, and the like. As usedherein, the terms “chelating agent” and “sequestrant” are synonymous.

As used herein, the term “free of chelating agent” refers to acomposition, mixture, or ingredients that do not contain a chelatingagent or sequestrant or to which a chelating agent or sequestrant hasnot been added. Should a chelating agent or sequestrant be presentthrough contamination of a composition, mixture, or ingredient that isfree of chelating agent, the amount of a chelating agent or sequestrantshall be less than 2 wt-%. In another embodiment, such an amount of achelating agent or sequestrant is less than 1 wt-%. In otherembodiments, such an amount of a chelating agent or sequestrant is lessthan 0.5 wt-% and in yet other embodiments, such an amount of achelating agent or sequestrant is less than 0.1 wt-%.

As used herein, the term “sanitizer” refers to an agent that reduces thenumber of bacterial contaminants to safe levels as judged by publichealth requirements. In an embodiment, sanitizers for use in thisinvention will provide at least a 99.999% reduction (5-log orderreduction). These reductions can be evaluated using a procedure set outin Germicidal and Detergent Sanitizing Action of Disinfectants, OfficialMethods of Analysis of the Association of Official Analytical Chemists,paragraph 960.09 and applicable sections, 15th Edition, 1990 (EPAGuideline 91-2). According to this reference a sanitizer should providea 99.999% reduction (5-log order reduction) within 30 seconds at roomtemperature, 25±2° C., against several test organisms.

As used herein, the term “disinfectant” refers to an agent that killsall vegetative cells including most recognized pathogenicmicroorganisms, using the procedure described in A.O.A.C. Use DilutionMethods, Official Methods of Analysis of the Association of OfficialAnalytical Chemists, paragraph 955.14 and applicable sections, 15thEdition, 1990 (EPA Guideline 91-2). As used herein, the term “high leveldisinfection” or “high level disinfectant” refers to a compound orcomposition that kills substantially all organisms, except high levelsof bacterial spores, and is effected with a chemical germicide clearedfor marketing as a sterilant by the Food and Drug Administration. Asused herein, the term “intermediate-level disinfection” or “intermediatelevel disinfectant” refers to a compound or composition that killsMycobacteria, most viruses, and bacteria with a chemical germicideregistered as a tuberculocide by the Environmental Protection Agency(EPA). As used herein, the term “low-level disinfection” or “low leveldisinfectant” refers to a compound or composition that kills someviruses and bacteria with a chemical germicide registered as a hospitaldisinfectant by the EPA.

As used in this invention, the term “sporicide” refers to a physical orchemical agent or process having the ability to cause greater than a 90%reduction (1-log order reduction) in the population of spores ofBacillus cereus or Bacillus subtilis within 10 seconds at 60° C. orwithin 60 seconds at 50° C. In certain embodiments, the sporicidalcompositions of the invention provide greater than a 99% reduction(2-log order reduction), greater than a 99.99% reduction (4-log orderreduction), or greater than a 99.999% reduction (5-log order reduction)in such population within 10 seconds at 60° C. or within 60 seconds at50° C.

Differentiation of antimicrobial “-cidal” or “-static” activity, thedefinitions which describe the degree of efficacy, and the officiallaboratory protocols for measuring this efficacy are considerations forunderstanding the relevance of antimicrobial agents and compositions.Antimicrobial compositions can affect two kinds of microbial celldamage. The first is a lethal, irreversible action resulting in completemicrobial cell destruction or incapacitation. The second type of celldamage is reversible, such that if the organism is rendered free of theagent, it can again multiply. The former is termed microbiocidal and thelater, microbiostatic. A sanitizer and a disinfectant are, bydefinition, agents which provide antimicrobial or microbiocidalactivity. In contrast, a preservative is generally described as aninhibitor or microbiostatic composition

As used herein, the term “alkyl” or “alkyl groups” refers to saturatedhydrocarbons having one or more carbon atoms, including straight-chainalkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,octyl, nonyl, decyl, etc.), cyclic alkyl groups (or “cycloalkyl” or“alicyclic” or “carbocyclic” groups) (e.g., cyclopropyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, etc.), branched-chain alkyl groups(e.g., isopropyl, tert-butyl, sec-butyl, isobutyl, etc.), andalkyl-substituted alkyl groups (e.g., alkyl-substituted cycloalkylgroups and cycloalkyl-substituted alkyl groups).

Unless otherwise specified, the term “alkyl” includes both“unsubstituted alkyls” and “substituted alkyls.” As used herein, theterm “substituted alkyls” refers to alkyl groups having substituentsreplacing one or more hydrogens on one or more carbons of thehydrocarbon backbone. Such substituents may include, for example,alkenyl, alkynyl, halogeno, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy,alkoxycarbonyloxy, aryloxy, aryloxycarbonyloxy, carboxylate,alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aminocarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl,phosphate, phosphonato, phosphinato, cyano, amino (including alkylamino, dialkylamino, arylamino, diarylamino, and alkylarylamino),acylamino (including alkylcarbonylamino, arylcarbonylamino, carbamoyland ureido), imino, sulfhydryl, alkylthio, arylthio, thiocarboxylate,sulfates, alkylsulfinyl, sulfonates, sulfamoyl, sulfonamido, nitro,trifluoromethyl, cyano, azido, heterocyclic, alkylaryl, or aromatic(including hetero aromatic) groups.

In some embodiments, substituted alkyls can include a heterocyclicgroup. As used herein, the term “heterocyclic group” includes closedring structures analogous to carbocyclic groups in which one or more ofthe carbon atoms in the ring is an element other than carbon, forexample, nitrogen, sulfur or oxygen. Heterocyclic groups may besaturated or unsaturated. Exemplary heterocyclic groups include, but arenot limited to, aziridine, ethylene oxide (epoxides, oxiranes), thiirane(episulfides), dioxirane, azetidine, oxetane, thietane, dioxetane,dithietane, dithiete, azolidine, pyrrolidine, pyrroline, oxolane,dihydrofuran, and furan.

As used herein the term, “consisting essentially of” in reference to acomposition refers to the listed ingredients and does not includeadditional ingredients that, if present, would affect the cleaning,disinfecting or sterilizing ability of the composition. The term“consisting essentially of” may also refer to a component of thecomposition. For instance, a surfactant package may consist essentiallyof two or more surfactants and such surfactant package would not includeany other ingredients that would affect the effectiveness of thatsurfactant package—either positively or negatively. As used herein theterm “consisting essentially of” in reference to a method of cleaningrefers to the listed steps and does not include additional steps (oringredients if a composition is included in the method) that, ifpresent, would affect the cleaning ability of the cleaning method.

The present invention contemplates the possibility of omitting anycomponents listed herein. The present invention further contemplates theomission of any components even though they are not expressly named asincluded or excluded from the invention.

Compounds of the Invention

The present invention relates, at least in part, tosulfoperoxycarboxylic acids, compositions thereof, and the use thereofin a variety of bleaching, disinfecting and cleaning applications. Thesulfoperoxycarboxylic acids of the present invention are also useful ascoupling agents. Further, certain compounds of the present invention canbe derived from non-petroleum based, renewable oils, e.g., castor, toll,soybean, canola, olive, peanut, tallow, rapeseed, and palm oils.

As used herein, the term “sulfoperoxycarboxylic acid,” “sulfonatedperacid,” or “sulfonated peroxycarboxylic acid” refers to theperoxycarboxylic acid form of a sulfonated carboxylic acid. In someembodiments, the sulfonated peracids of the present invention aremid-chain sulfonated peracids. As used herein, the term “mid-chainsulfonated peracid” refers to a peracid compound that includes asulfonate group attached to a carbon that is at least one carbon (e.g.,the three position or further) from the carbon of the percarboxylic acidgroup in the carbon backbone of the percarboxylic acid chain, whereinthe at least one carbon is not in the terminal position. As used herein,the term “terminal position,” refers to the carbon on the carbonbackbone chain of a percarboxylic acid that is furthest from thepercarboxyl group.

Without wishing to be bound by any particular theory, it is thought thatmid-chain sulfonated peracids, e.g., mid-chain sulfonated peracids witha C10-C18 carbon backbone have a substantially greater solubilitycompared to terminally sulfonated peracids of a similar chain length,even at an acidic pH. For example, at a pH of 4, the terminallysulfonated peracid, 11-sulfoundecane peroxoic acid has a relatively lowsolubility of about 1.3%. At the same pH, the mid chain sulfonatedperacid, persulfonated oleic acid has a solubility of greater than about50%. This is unexpected as an increase in peracid chain length isthought to lead to a decrease in solubility. The issue of low solubilitywhen using long chain peracids has been addressed by increasing the pHto above 7. However, at increased pH antimicrobial efficacy issubstantially reduced. Further, bleaching efficacy decreasesproportionally with every pH unit increase over about 7. Thus,solubility at an acidic pH (lower than about 7) is beneficial to themid-chain sulfonated peracids of the present invention.

The sulfoperoxycarboxylic acids of the present invention can be usedalone, or can be combined with additional ingredients. In someembodiments, compositions of the present invention can include one ormore of the sulfoperoxycarboxylic acids of the present invention.

Peroxycarboxylic (or percarboxylic) acids generally have the formulaR(CO₃H)_(n), where, for example, R is an alkyl, arylalkyl, cycloalkyl,aromatic, or heterocyclic group, and n is one, two, or three, and namedby prefixing the parent acid with peroxy. Percarboxylic acids can bemade by the direct, acid catalyzed equilibrium action of hydrogenperoxide with the carboxylic acid, by autooxidation of aldehydes, orfrom acid chlorides, and hydrides, or carboxylic anhydrides withhydrogen or sodium peroxide. The R group can be saturated or unsaturatedas well as substituted or unsubstituted.

The chemical structures herein are drawn according to the conventionalstandards known in the art. Thus, where an atom, such as a carbon atom,as drawn appears to have an unsatisfied valency, then that valency isassumed to be satisfied by a hydrogen atom, even though that hydrogenatom is not necessarily explicitly drawn. The structures of some of thecompounds of this invention include stereogenic carbon atoms. It is tobe understood that isomers arising from such asymmetry (e.g., allenantiomers and diastereomers) are included within the scope of thisinvention unless indicated otherwise. That is, unless otherwisestipulated, any chiral carbon center may be of either (R)- or(S)-stereochemistry. Such isomers can be obtained in substantially pureform by classical separation techniques and bystereochemically-controlled synthesis. Furthermore, alkenes can includeeither the E- or Z-geometry, where appropriate. In addition, thecompounds of the present invention may exist in unsolvated as well assolvated forms with acceptable solvents such as water, THF, ethanol, andthe like. In general, the solvated forms are considered equivalent tothe unsolvated forms for the purposes of the present invention.

In some aspects, the present invention pertains to sulfoperoxycarboxylicacids of Formula I:

wherein R₁ is hydrogen, or a substituted or unsubstituted alkyl group;

R₂ is a substituted or unsubstituted alkyl group;

X is hydrogen, a cationic group, or an ester forming moiety;

or salts or esters thereof.

In some embodiments, R₁ is a substituted or unsubstituted C_(m) alkylgroup; X is hydrogen a cationic group, or an ester forming moiety; R₂ isa substituted or unsubstituted C_(n) alkyl group; m=1 to 10; n=1 to 10;and m+n is less than 18, or salts, esters or mixtures thereof.

In some embodiments, R₁ is hydrogen. In other embodiments, R₁ is asubstituted or unsubstituted alkyl group. In some embodiments, R₁ is asubstituted or unsubstituted alkyl group that does not include a cyclicalkyl group. In some embodiments, R₁ is a substituted alkyl group. Insome embodiments, R₁ is an unsubstituted C₁-C₉ alkyl group. In someembodiments, R₁ is an unsubstituted C₇ or C₈ alkyl. In otherembodiments, R₁ is a substituted C₈-C₁₀ alkyl group. In someembodiments, R₁ is a substituted C₈-C₁₀ alkyl group is substituted withat least 1, or at least 2 hydroxyl groups. In still yet otherembodiments, R₁ is a substituted C₁-C₉ alkyl group. In some embodiments,R₁ is a substituted C₁-C₉ substituted alkyl group is substituted with atleast 1 SO₃H group.

In other embodiments, R₁ is a C₉-C₁₀ substituted alkyl group. In someembodiments, R₁ is a substituted C₉-C₁₀ alkyl group wherein at least twoof the carbons on the carbon backbone form a heterocyclic group. In someembodiments, the heterocyclic group is an epoxide group.

In some embodiments, R₂ is a substituted C₁ to C₁₀ alkyl group. In someembodiments, R₂ is a substituted C₈-C₁₀ alkyl. In some embodiments, R₂is an unsubstituted C₆-C₉ alkyl. In other embodiments, R₂ is a C₈ to C₁₀alkyl group substituted with at least one hydroxyl group. In someembodiments, R₂ is a C₁₀ alkyl group substituted with at least twohydroxyl groups. In other embodiments, R₂ is a C₈ alkyl groupsubstituted with at least one SO₃H group. In some embodiments, R₂ is asubstituted C₉ group, wherein at least two of the carbons on the carbonbackbone form a heterocyclic group. In some embodiments, theheterocyclic group is an epoxide group. In some embodiments, R₁ is aC₈-C₉ substituted or unsubstituted alkyl, and R₂ is a C₇-C₈ substitutedor unsubstituted alkyl.

In some embodiments, the compound of the invention is selected from thegroup consisting of:

salts, esters, and mixtures and derivatives thereof.

In other embodiments, the compound of the invention is selected from thegroup consisting of:

and mixtures and derivatives thereof.Compounds of the invention are also shown in Table 1 below.

TABLE 1 Sulfonated Peroxyacid Compounds ID Structure/Name of Compound A

B

C

D

E

F

G

H

I

J

K

L

M

N

O

In some embodiments, the starting material for the preparation of thecompounds of the present invention is a sulfonated fatty acid. Withoutwishing to be bound by any particular theory, it is thought that thesulfo-group is inert in an oxidative environment. Further, it is thoughtthat the hydrophility of the sulfo-group is not as impacted by pH asother substituents. In some embodiments, the sulfonated percarboxylicacids of the present invention are formed from commercially availablesulfonated fatty acids. In other embodiments, the compounds of thepresent invention are formed from commercially available non-sulfonatedfatty acids, which can be sulfonated. In some embodiments, the startingfatty acid will be sulfonated prior to conversion to a peroxycarboxylicacid. In other embodiments, the starting fatty acid will be sulfonatedat the same time or after the formation of the peroxycarboxylic acid.Sulfonated fatty acids suitable for use in forming compounds of thepresent invention include, but are not limited to, 11-sulfoundecanoicacid, 10,11-disulfoundecanoic acid, sulfonated oleic acid, sulfonatedlinoleic acid, sulfonated palmitoleic acid and sulfonated stearic acid.

Without wishing to be bound by any particular theory, it is thought thatthe peracid formed from certain commercially available sulfonated oleicacid starting materials includes a mixture of the compounds of thepresent invention. It is thought that this is due, in part, to thenature of the sulfonated oleic acid starting material. That is, it isthought that because the sulfonated oleic acid starting material isderived from naturally occurring sources, it is not chemically pure,i.e., does not contain only one form of the sulfonated oleic acid. Thus,without wishing to be bound by any particular theory it is thought thatsulfonated peroleic acid formed (hereinafter referred to as the“sulfonated peroleic acid product”) can include a mixture of CompoundsA, N, I, and O as the primary components. Without wishing to be bound byany particular theory it is thought that in some embodiments, thesulfonated peroleic acid product includes about 20-25 wt % Compound A(10-Hydroxy-9-sulfooctadecaneperoxoic acid) about 20-25 wt % Compound N(10,11-dihydroxy-9-sulfooctadecaneperoxoic acid), about 20-25 wt %Compound I (9-Hydroxy-10-sulfooctadecaneperoxoic acid), and about 20-25wt % Compound O (8,9-dihydroxy-10-sulfooctadecaneperoxoic acid). Theremainder of the product is thought to include about 5 to about 10 wt %of a mixture of these compounds.

The sulfoperoxyacids can be formed using a variety of reactionmechanisms. For example, in some embodiments, the peracids are formed bythe direct acid catalyzed equilibrium action of hydrogen peroxide withthe starting materials.

In some embodiments, the sulfonated carboxylic acids for use in formingthe compounds of the present invention are not sulfonated at the αposition. As used herein, the term “α position” refers to the carbon onthe carbon backbone of the percarboxylic acid chain that is directlyconnected to, viz. immediately next to, the carboxylic acid group. Ithas been found that having the sulfonate group at the α position of thefatty acid prohibits the oxidation and/or perhydrolysis of thecarboxylic acid group to form the corresponding peroxycarboxylic acid.Without wishing to be bound by any particular theory, it is thought thatthe α-sulfo group makes the carboxylic acid group on the fatty acidelectronically deficient, and thus oxidation and/or perhydrolysis andformation of the corresponding percarboxylic acid requires extremely lowpHs. Upon neutralization or even moderate elevation of these pHs, it isthought that the peracids very rapidly hydrolyze back to the parentacids, rendering them impractical for most applications.

Sulfonated Peroxycarboxylic Acid Compositions

In some aspects, the present invention relates to compositions includinga sulfonated peroxycarboxylic acid compound, or mixture thereof, ofFormula I. The compositions of the present invention can be used asdetergent and/or bleaching compositions for a variety of substrates andsurfaces, e.g., woven or non-woven textiles, hard surfaces. Thecompositions of the present invention can also be used as sanitizing ordisinfectant or sterilizing or sporicidal or for other antimicrobialpurposes. Further, compounds of the present invention can be used ascoupling agents in compositions for various applications, e.g., foodcontact sanitizing, hard surface disinfection, textile disinfection. Insome embodiments, compositions containing compounds of the presentinvention can be multipurpose. That is, the compositions of the presentinvention can, for example, act as multipurpose combination systems;including, antimicrobials and detergents and bleaches, or as bothcoupling agents and antimicrobials and bleaches, and detergent andbleaching mixtures, and the like.

The compositions of the present invention also show enhanced stabilitycompared to conventional peroxygen containing compositions. In someembodiments, the compositions of the present invention are stable for atleast about 1 year at room temperature. In some embodiments, thecompositions of the present invention are stable at about 100° F. for atleast 30 days. In other embodiments, the compositions of the presentinvention are stable at about 140° F. for at least 30 days. For example,11-sulfoundecanoic peroxyacid (Compound D) is stable as a powder systemat about 140° F. for at least 30 days.

The compositions of the present invention have no or low odor. Forexample, in some embodiments, compositions of the present invention havean odor less unpleasant than (e.g., as measured by an hedonic tonerating) than 5, 4, 3, 2, or 1 wt-% acetic acid in water. In otherembodiments, the compositions of the present invention have no odordetectable by a user.

In some embodiments, the compositions of the present invention include asulfonated peracid or mixture thereof of Formula I, and at least oneadditional ingredient. Additional ingredients suitable for use with thecompositions of the present invention include, but are not limited to,oxidizing agents, carboxylic acids, surfactants, stabilizing agents(e.g., metal chelators), and mixtures thereof. The compounds andcompositions of the invention can also be used in conjunction withconventional cleaning agents, e.g., alkaline detergents.

In some embodiments, the compositions of the present invention can beused as a sanitizing composition for articles cleaned using a clean inplace (CIP) technique. Such compositions can include an oxidizing agent,a stabilizing agent, an acidulant and a surfactant or mixture thereof,in the following concentrations.

TABLE A Concentrate CIP Sanitizer by Weight % Oxidizing Agent 0.1-10 2-85-7 Stabilizing Agent 0.1-10 0.5-5   1-2 Acidulant   0-50 10-40 20-30Surfactant   0-50 10-40 25-35

In other embodiments, the compositions of the present invention can beused as a textile disinfectant/sanitizer. Such compositions can includeoxidizing agent, stabilizing agent and a carboxylic acid in thefollowing concentrations.

TABLE B Concentrate Textile Disinfectant/Sanitizer by Weight % OxidizingAgent 10-75 25-60 30-50 Stabilizing Agent 0.1-10  0.5-5   2-4 CarboxylicAcid  1-40 10-30 20-25

In other embodiments, the compositions of the present invention can beused as a textile combined cleaning, bleaching, and disinfectant. Suchcompositions can include oxidizing agent, stabilizing agent, carboxylicacid, surfactant, bleach, acidulant, and viscosity reducing agent in thefollowing concentrations.

TABLE C Concentrate Textile Detergent/Bleach/Disinfectant by Weight %Oxidizing Agent 0.1-75 2-40 5-30 Stabilizing Agent 0.01-10  0.05-5   0.08-2    Bleach 0.05-75  0.10-30   1.0-20   Carboxylic Acid 0.1-400.5-30   1-20 Surfactant 0.5-70 2-50 10-35  Viscosity Reducing   0-200.5-15   1-10 AgentOxidizing Agents

In some aspects, the compositions of the present invention include acompound of Formula I. In some embodiments, the compositions of thepresent invention further include at least one oxidizing agent. In someembodiments, the compositions of the present invention are substantiallyfree of an oxidizing agent. When present, the present composition caninclude any of a variety of oxidizing agents, for example, hydrogenperoxide and/or any inorganic or organic peroxide or peracid. Theoxidizing agent can be present at an amount effective to convert asulfonated carboxylic acid to a sulfonated peroxycarboxylic acid. Insome embodiments, the oxidizing agent can also have antimicrobialactivity. In other embodiments, the oxidizing agent is present in anamount insufficient to exhibit antimicrobial activity.

In some embodiments, the compositions of the present invention includeabout 0.001 wt % oxidizing agent to about 99 wt % oxidizing agent. Inother embodiments, the compositions of the present invention includeabout 1 wt % to about 60 wt % oxidizing agent. In some embodiments, thecompositions of the invention include about 50 wt % to about 80 wt %oxidizing agent. In other embodiments, the compositions of the inventioninclude about 15 wt % to about 30 wt % oxidizing agent. In yet otherembodiments, the compositions of the present invention include about 25wt % oxidizing agent. It is to be understood that all ranges and valuesbetween these ranges and values are encompassed by the presentinvention.

Examples of inorganic oxidizing agents include the following types ofcompounds or sources of these compounds, or alkali metal salts includingthese types of compounds, or forming an adduct therewith: hydrogenperoxide, urea-hydrogen peroxide complexes or hydrogen peroxide donorsof: group 1 (IA) oxidizing agents, for example lithium peroxide, sodiumperoxide; group 2 (IIA) oxidizing agents, for example magnesiumperoxide, calcium peroxide, strontium peroxide, barium peroxide; group12 (IIB) oxidizing agents, for example zinc peroxide; group 13 (IIIA)oxidizing agents, for example boron compounds, such as perborates, forexample sodium perborate hexahydrate of the formulaNa₂[B₂(O₂)₂(OH)₄].6H₂O (also called sodium perborate tetrahydrate);sodium peroxyborate tetrahydrate of the formula Na₂B₂(O₂)₂[(OH)₄].4H₂O(also called sodium perborate trihydrate); sodium peroxyborate of theformula Na₂[B₂(O₂)₂(OH)₄] (also called sodium perborate monohydrate);group 14 (IVA) oxidizing agents, for example persilicates andperoxycarbonates, which are also called percarbonates, such aspersilicates or peroxycarbonates of alkali metals; group 15 (VA)oxidizing agents, for example peroxynitrous acid and its salts;peroxyphosphoric acids and their salts, for example, perphosphates;group 16 (VIA) oxidizing agents, for example peroxysulfuric acids andtheir salts, such as peroxymonosulfuric and peroxydisulfuric acids, andtheir salts, such as persulfates, for example, sodium persulfate; andgroup VIIa oxidizing agents such as sodium periodate, potassiumperchlorate. Other active inorganic oxygen compounds can includetransition metal peroxides; and other such peroxygen compounds, andmixtures thereof.

Examples of organic oxidizing agents include, but are not limited to,perbenzoic acid, derivatives of perbenzoic acid, t-butyl benzoylhydroperoxide, benzoyl hydroperoxide, or any other organic basedperoxide and mixtures thereof, as well as sources of these compounds.Other examples include, but are not limited to, peracids includingC1-C12 percarboxylic acids such as peracetic acid, performic acid,percarbonic acid, peroctanoic acid, and the like; per-diacids orper-triacids such as peroxalic acid, persuccinic acid, percitric acid,perglycolic acid, permalic acid and the like; and aromatic peracids suchas perbenzoic acid, or mixtures thereof.

In some embodiments, the compositions of the present invention employone or more of the inorganic oxidizing agents listed above. Suitableinorganic oxidizing agents include ozone, hydrogen peroxide, hydrogenperoxide adduct, group IIIA oxidizing agent, or hydrogen peroxide donorsof group VIA oxidizing agent, group VA oxidizing agent, group VIIAoxidizing agent, or mixtures thereof. Suitable examples of suchinorganic oxidizing agents include percarbonate, perborate, persulfate,perphosphate, persilicate, or mixtures thereof.

Carboxylic and Percarboxylic Acids

In some embodiments, the compositions of the present invention includeat least one sulfoperoxycarboxylic acid of the present invention, and atleast one carboxylic and/or percarboxylic acid. In some embodiments, thecompositions of the present invention include at least two, at leastthree, or at least four or more carboxylic and/or percarboxylic acids.

In some embodiments, the carboxylic acid for use with the compositionsof the present invention includes a C₁ to C₂₂ carboxylic acid. In someembodiments, the carboxylic acid for use with the compositions of thepresent invention is a C₅ to C₁₁ carboxylic acid. In some embodiments,the carboxylic acid for use with the compositions of the presentinvention is a C₁ to C₄ carboxylic acid. Examples of suitable carboxylicacids include, but are not limited to, formic, acetic, propionic,butanoic, pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic,undecanoic, dodecanoic, as well as their branched isomers, lactic,maleic, ascorbic, citric, hydroxyacetic, neopentanoic, neoheptanoic,neodecanoic, oxalic, malonic, succinic, glutaric, adipic, pimelic subricacid, and mixtures thereof.

In some embodiments, the compositions of the present invention includeabout 0.1 wt % to about 80 wt % of a carboxylic acid. In otherembodiments, the compositions of the present invention include about 1wt % to about 60 wt % of a carboxylic acid. In yet other embodiments,the compositions of the present invention include about 20 wt %, about30 wt %, or about 40 wt % of a carboxylic acid. In some embodiments, thecompositions of the present invention include about 5 wt % to about 10wt % of acetic acid. In other embodiments, the compositions of thepresent invention include about 5 wt % to about 10 wt % of octanoicacid. In other embodiments, the compositions of the present inventioninclude a combination of octanoic acid and acetic acid.

In some embodiments, the compositions of the present invention include acompound of Formula I, and at least one peroxycarboxylic acid.Peroxycarboxylic acids useful in the compositions and methods of thepresent invention include peroxyformic, peroxyacetic, peroxypropionic,peroxybutanoic, peroxypentanoic, peroxyhexanoic, peroxyheptanoic,peroxyoctanoic, peroxynonanoic, peroxydecanoic, peroxyundecanoic,peroxydodecanoic, or the peroxyacids of their branched chain isomers,peroxylactic, peroxymaleic, peroxyascorbic, peroxyhydroxyacetic,peroxyoxalic, peroxymalonic, peroxysuccinic, peroxyglutaric,peroxyadipic, peroxypimelic and peroxysubric acid and mixtures thereof.In some embodiments, the compositions of the invention utilize acombination of several different peroxycarboxylic acids. For example, insome embodiments, the composition includes one or more C₁ to C₄peroxycarboxylic acids and one or more C₅ to C₁₁ peroxycarboxylic acids.In some embodiments, the C₁ to C₄ peroxycarboxylic acid is peroxyaceticacid and the C₅ to C₁₁ acid is peroxyoctanoic acid.

In some embodiments, the compositions of the present invention includeperoxyacetic acid. Peroxyacetic (or peracetic) acid is aperoxycarboxylic acid having the formula: CH₃COOOH. Generally,peroxyacetic acid is a liquid having an acrid odor at higherconcentrations and is freely soluble in water, alcohol, ether, andsulfuric acid. Peroxyacetic acid can be prepared through any number ofmethods known to those of skill in the art including preparation fromacetaldehyde and oxygen in the presence of cobalt acetate. A solution ofperoxyacetic acid can be obtained by combining acetic acid with hydrogenperoxide. A 50% solution of peroxyacetic acid can be obtained bycombining acetic anhydride, hydrogen peroxide and sulfuric acid.

In some embodiments, the compositions of the present invention includeperoxyoctanoic acid, peroxynonanoic acid, or peroxyheptanoic acid. Insome embodiments, the compositions include peroxyoctanoic acid.Peroxyoctanoic (or peroctanoic) acid is a peroxycarboxylic acid havingthe formula, for example, of n-peroxyoctanoic acid: CH₃(CH₂)₆COOOH.Peroxyoctanoic acid can be an acid with a straight chain alkyl moiety,an acid with a branched alkyl moiety, or a mixture thereof.Peroxyoctanoic acid can be prepared through any number of methods knownto those of skill in the art. A solution of peroxyoctanoic acid can beobtained by combining octanoic acid and hydrogen peroxide and ahydrotrope, solvent or carrier.

In some embodiments, the compositions of the present invention includeabout 0.1 wt % to about 90 wt % of one or more peroxycarboxylic acids.In other embodiments, the compositions of the present invention includeabout 1 wt % to about 25 wt % of one or more peroxycarboxylic acids. Inyet other embodiments, the compositions of the present invention includeabout 5 wt % to about 10 wt % of one or more peroxycarboxylic acids. Insome embodiments, the compositions of the present invention includeabout 1 wt % to about 25 wt % of peroxyacetic acid. In otherembodiments, the compositions of the present invention include about 0.1wt % to about 10 wt % of peroxyoctanoic acid. In still yet otherembodiments, the compositions of the present invention include a mixtureof about 5 wt % peroxyacetic acid, and about 1.5 wt % peroxyoctanoicacid.

Surfactants

In some embodiments, the compositions of the present invention include asurfactant. Surfactants suitable for use with the compositions of thepresent invention include, but are not limited to, nonionic surfactants,anionic surfactants, and zwitterionic surfactants. In some embodiments,the compositions of the present invention include about 10 wt % to about50 wt % of a surfactant. In other embodiments the compositions of thepresent invention include about 15 wt % to about 30% of a surfactant. Instill yet other embodiments, the compositions of the present inventioninclude about 25 wt % of a surfactant. In some embodiments, thecompositions of the present invention include about 100 ppm to about1000 ppm of a surfactant.

Nonionic Surfactants

Suitable nonionic surfactants suitable for use with the compositions ofthe present invention include alkoxylated surfactants. Suitablealkoxylated surfactants include alkoxylates made from ethylene (EO),propylene (PO), and butylene (BO) oxides. Suitable alkoxylatedsurfactants include homo or copolymers or terpolymers, capped EO/PO/BOcopolymers, alcohol alkoxylates, capped alcohol alkoxylates, mixturesthereof, or the like. Suitable alkoxylated surfactants for use assolvents include EO/PO block copolymers, such as the Pluronic andreverse Pluronic surfactants; alcohol alkoxylates, such as Dehypon LS-54(R-(EO)₅(PO)₄) and Dehypon LS-36 (R-(EO)₃(PO)₆); and capped alcoholalkoxylates, such as Plurafac LF221 and Tegoten EC11; mixtures thereof,or the like. More specifically the composition of the present inventioncan include alkoxylated primary or secondary alcohol having from 8 to 18carbon atoms reacted with from 2 to 12 moles of ethylene, and/orpropylene, and/or butylene oxide. In an embodiment the nonionic has from3 to 18 moles of alkylene oxides, in another embodiment from 3 to about10 moles of ethylene oxide, and in yet another embodiment about 7 molesof EO. These materials are commercially available and well-knownnonionic surfactants. The following materials are useful: lauryl alcoholethoxylated with 3 moles of ethylene oxide (EO), coco alcoholethoxylated with 3 moles EO, stearyl alcohol ethoxylated with 5 molesEO, mixed C₁₂-C₁₅ alcohol ethoxylated with 7 moles EO, mixed secondaryC₁₁-C₁₅ alcohol ethoxylated with 7 moles EO, mixed C₉-C₁₁ linear alcoholethoxylated with 6 moles EO and the like. In an embodiment the nonionichas from 8 to 15 carbon atoms in the alkyl group. When this alkyl groupis used a nonionic is the mixed C₁₂-C₁₅ alcohol ethoxylated with 7 molesEO. In an embodiment it comprises the alcohol alkoxylates, particularlythe alcohol ethoxylates and propoxylates, especially the mixedethoxylates and propoxylates, particularly with 3-7 oxyethylene (EO)units and 3-7 oxypropylene (PO) units such as the alcohol Dehypon™available from Cognis Corporation, having 5 EO units and 4 PO units.These materials may be present in a wide range of concentrations, suchas, for example, from 0.1 to 25% by weight of the concentrate orsolution, from 1 to 25% by weight of the concentrate or solution, 1 to20% by weight of the concentrate or solution, 2 to 15% by weight of theconcentrate or solution, or 4 to 12% by weight of the concentrate orsolution.

Nonionic surfactants include synthetic or natural alcohols that arealkoxylated (with ethylene and/or propylene and/or butylenes oxide) toyield a variety of C₆-C₂₄ alcohol ethoxylates and/or propoxylates and/orbutoxylates (preferably C₆-C₁₄ alcohol ethoxylates and/or propoxylatesand/or butoxylates having 1 to about 20 alkylene oxide groups(preferably about 9 to about 20 alkylene oxide groups); C₆-C₂₄alkylphenol ethoxylates (preferably C₈-C₁₀ alkylphenol ethoxylates)having 1 to about 100 ethylene oxide groups (preferably about 12 toabout 20 ethylene oxide groups); and C₆-C₂₄ alkylpolyglycosides(preferably C₆-C₂₀ alkylpolyglycosides) having 1 to about 20 glycosidegroups (preferably about 9 to about 20 glycoside groups).

Semi-Polar Nonionic Surfactants

The semi-polar type of nonionic surface active agents are another classof nonionic surfactant useful in compositions of the present invention.Semi-polar nonionic surfactants include the amine oxides, phosphineoxides, sulfoxides and their alkoxylated derivatives.

Amine oxides are tertiary amine oxides corresponding to the generalformula:

wherein the arrow is a conventional representation of a semi-polar bond;and, R¹, R², and R³ may be aliphatic, aromatic, heterocyclic, alicyclic,or combinations thereof. Generally, for amine oxides of detergentinterest, R¹ is an alkyl radical of from about 8 to about 24 carbonatoms; R² and R³ are alkyl or hydroxyalkyl of 1-3 carbon atoms or amixture thereof; R² and R³ can be attached to each other, e.g. throughan oxygen or nitrogen atom, to form a ring structure; R⁴ is an alkyleneor a hydroxyalkylene group containing 2 to 3 carbon atoms; and n rangesfrom 0 to about 20. An amine oxide can be generated from thecorresponding amine and an oxidizing agent, such as hydrogen peroxide.

Useful water soluble amine oxide surfactants are selected from theoctyl, decyl, dodecyl, isododecyl, coconut, or tallow alkyl di-(loweralkyl) amine oxides, specific examples of which are octyldimethylamineoxide, nonyldimethylamine oxide, decyldimethylamine oxide,undecyldimethylamine oxide, dodecyldimethylamine oxide,iso-dodecyldimethyl amine oxide, tridecyldimethylamine oxide,tetradecyldimethylamine oxide, pentadecyldimethylamine oxide,hexadecyldimethylamine oxide, heptadecyldimethylamine oxide,octadecyldimethylaine oxide, dodecyldipropylamine oxide,tetradecyldipropylamine oxide, hexadecyldipropylamine oxide,tetradecyldibutylamine oxide, octadecyldibutylamine oxide,bis(2-hydroxyethyl)dodecylamine oxide,bis(2-hydroxyethyl)-3-dodecoxy-1-hydroxypropylamine oxide,dimethyl-(2-hydroxydodecyl)amine oxide, 3,6,9-trioctadecyldimethylamineoxide and 3-dodecoxy-2-hydroxypropyldi-(2-hydroxyethyl)amine oxide.

Anionic Surfactants

Anionic sulfate surfactants suitable for use in the present compositionsinclude alkyl ether sulfates, alkyl sulfates, the linear and branchedprimary and secondary alkyl sulfates, alkyl ethoxysulfates, fatty oleylglycerol sulfates, alkyl phenol ethylene oxide ether sulfates, theC₅-C₁₇ acyl-N—(C₁-C₄ alkyl) and —N—(C₁-C₂ hydroxyalkyl) glucaminesulfates, and sulfates of alkylpolysaccharides such as the sulfates ofalkylpolyglucoside, and the like. Also included are the alkyl sulfates,alkyl poly(ethyleneoxy)ether sulfates and aromatic poly(ethyleneoxy)sulfates such as the sulfates or condensation products of ethylene oxideand nonyl phenol (usually having 1 to 6 oxyethylene groups permolecule).

Anionic sulfonate surfactants suitable for use in the presentcompositions also include alkyl sulfonates, the linear and branchedprimary and secondary alkyl sulfonates, and the aromatic sulfonates withor without substituents; including alkylbenzene sulfonates.

Anionic carboxylate surfactants suitable for use in the presentcompositions include carboxylic acids (and salts), such as alkanoicacids (and alkanoates), ester carboxylic acids (e.g. alkyl succinates),ether carboxylic acids, and the like. Such carboxylates include alkylethoxy carboxylates, alkyl aryl ethoxy carboxylates, alkyl polyethoxypolycarboxylate surfactants and soaps (e.g. alkyl carboxyls). Secondarycarboxylates useful in the present compositions include those whichcontain a carboxyl unit connected to a secondary carbon. The secondarycarbon can be in a ring structure, e.g. as in p-octyl benzoic acid, oras in alkyl-substituted cyclohexyl carboxylates. The secondarycarboxylate surfactants typically contain no ether linkages, no esterlinkages and no hydroxyl groups. Further, they typically lack nitrogenatoms in the head-group (amphiphilic portion). Suitable secondary soapsurfactants typically contain 11-13 total carbon atoms, although morecarbons atoms (e.g., up to 16) can be present. Suitable carboxylatesalso include acylamino acids (and salts), such as acylgluamates, acylpeptides, sarcosinates (e.g. N-acyl sarcosinates), taurates (e.g. N-acyltaurates and fatty acid amides of methyl tauride), and the like.

Suitable anionic surfactants include alkyl or alkylaryl ethoxycarboxylates of the following formula:R—O—(CH₂CH₂O)_(n)(CH₂)_(m)—CO₂X  (3)in which R is a C₈ to C₂₂ alkyl group or

in which R¹ is a C₄-C₁₆ alkyl group; n is an integer of 1-20; m is aninteger of 1-3; and X is a counter ion, such as hydrogen, sodium,potassium, lithium, ammonium, or an amine salt such as monoethanolamine,diethanolamine or triethanolamine. In some embodiments, n is an integerof 4 to 10 and m is 1. In some embodiments, R is a C₈-C₁₆ alkyl group.In some embodiments, R is a C₁₂-C₁₄ alkyl group, n is 4, and m is 1.

In other embodiments, R is

and R¹ is a C₆-C₁₂ alkyl group. In still yet other embodiments, R¹ is aC₉ alkyl group, n is 10 and m is 1.

Such alkyl and alkylaryl ethoxy carboxylates are commercially available.These ethoxy carboxylates are typically available as the acid forms,which can be readily converted to the anionic or salt form. Commerciallyavailable carboxylates include, Neodox 23-4, a C₁₂₋₁₃ alkyl polyethoxy(4) carboxylic acid (Shell Chemical), and Emcol CNP-110, a C₉ alkylarylpolyethoxy (10) carboxylic acid (Witco Chemical). Carboxylates are alsoavailable from Clariant, e.g. the product Sandopan® DTC, a C₁₃ alkylpolyethoxy (7) carboxylic acid.

Anionic surfactants include C₆-C₂₄ alkylbenzene sulfonates; C₆-C₂₄olefin sulfonates; C₆-C₂₄ paraffin sulfonates; cumene sulfonate; xylenesulfonate; C₆-C₂₄ alcohol sulfates (preferably C₆-C₁₂ alcohol sulfates);and C₆-C₂₄ alcohol ether sulfates having 1 to about 20 ethylene oxidegroups.

Amphoteric Surfactants

Amphoteric, or ampholytic, surfactants contain both a basic and anacidic hydrophilic group and an organic hydrophobic group. These ionicentities may be any of anionic or cationic groups described herein forother types of surfactants. A basic nitrogen and an acidic carboxylategroup are the typical functional groups employed as the basic and acidichydrophilic groups. In a few surfactants, sulfonate, sulfate,phosphonate or phosphate provide the negative charge.

Amphoteric surfactants can be broadly described as derivatives ofaliphatic secondary and tertiary amines, in which the aliphatic radicalmay be straight chain or branched and wherein one of the aliphaticsubstituents contains from about 8 to 18 carbon atoms and one containsan anionic water solubilizing group, e.g., carboxy, sulfo, sulfato,phosphato, or phosphono. Amphoteric surfactants are subdivided into twomajor classes known to those of skill in the art and described in“Surfactant Encyclopedia” Cosmetics & Toiletries, Vol. 104 (2) 69-71(1989). The first class includes acyl/dialkyl ethylenediaminederivatives (e.g. 2-alkyl hydroxyethyl imidazoline derivatives) andtheir salts. The second class includes N-alkylamino acids and theirsalts. Some amphoteric surfactants can be envisioned as fitting intoboth classes.

Amphoteric surfactants can be synthesized by methods known to those ofskill in the art. For example, 2-alkyl hydroxyethyl imidazoline issynthesized by condensation and ring closure of a long chain carboxylicacid (or a derivative) with dialkyl ethylenediamine. Commercialamphoteric surfactants are derivatized by subsequent hydrolysis andring-opening of the imidazoline ring by alkylation—for example withchloroacetic acid or ethyl acetate. During alkylation, one or twocarboxy-alkyl groups react to form a tertiary amine and an ether linkagewith differing alkylating agents yielding different tertiary amines.

Long chain imidazole derivatives having application in the presentinvention generally have the general formula:

wherein R is an acyclic hydrophobic group containing from about 8 to 18carbon atoms and M is a cation to neutralize the charge of the anion,generally sodium. Commercially prominent imidazoline-derived amphotericsthat can be employed in the present compositions include for example:Cocoamphopropionate, Cocoamphocarboxy-propionate, Cocoamphoglycinate,Cocoamphocarboxy-glycinate, Cocoamphopropyl-sulfonate, andCocoamphocarboxy-propionic acid. Amphocarboxylic acids can be producedfrom fatty imidazolines in which the dicarboxylic acid functionality ofthe amphodicarboxylic acid is diacetic acid and/or dipropionic acid.

The carboxymethylated compounds (glycinates) described herein abovefrequently are called betaines. Betaines are a special class ofamphoteric discussed herein below in the section entitled, ZwitterionSurfactants.

Long chain N-alkylamino acids are readily prepared by reaction RNH₂, inwhich R═C₈-C₁₈ straight or branched chain alkyl, fatty amines withhalogenated carboxylic acids. Alkylation of the primary amino groups ofan amino acid leads to secondary and tertiary amines. Alkyl substituentsmay have additional amino groups that provide more than one reactivenitrogen center. Most commercial N-alkylamine acids are alkylderivatives of beta-alanine or beta-N(2-carboxyethyl) alanine. Examplesof commercial N-alkylamino acid ampholytes having application in thisinvention include alkyl beta-amino dipropionates, RN(C₂H₄COOM)₂ andRNHC₂H₄COOM. In an embodiment, R can be an acyclic hydrophobic groupcontaining from about 8 to about 18 carbon atoms, and M is a cation toneutralize the charge of the anion.

Suitable amphoteric surfactants include those derived from coconutproducts such as coconut oil or coconut fatty acid. Additional suitablecoconut derived surfactants include as part of their structure anethylenediamine moiety, an alkanolamide moiety, an amino acid moiety,e.g., glycine, or a combination thereof; and an aliphatic substituent offrom about 8 to 18 (e.g., 12) carbon atoms. Such a surfactant can alsobe considered an alkyl amphodicarboxylic acid. These amphotericsurfactants can include chemical structures represented as:C₁₋₂-alkyl-C(O)—NH—CH₂—CH₂—N⁺(CH₂—CH₂—CO₂Na)₂—CH₂—CH₂—OH orC₁₂-alkyl-C(O)—N(H)—CH₂—CH₂—N⁺(CH₂—CO₂Na)₂—CH₂—CH₂—OH. Disodiumcocoampho dipropionate is one suitable amphoteric surfactant and iscommercially available under the tradename Miranol™ FBS from RhodiaInc., Cranbury, N.J. Another suitable coconut derived amphotericsurfactant with the chemical name disodium cocoampho diacetate is soldunder the tradename Mirataine™ JCHA, also from Rhodia Inc., Cranbury,N.J.

A typical listing of amphoteric classes, and species of thesesurfactants, is given in U.S. Pat. No. 3,929,678 issued to Laughlin andHeuring on Dec. 30, 1975. Further examples are given in “Surface ActiveAgents and Detergents” (Vol. I and II by Schwartz, Perry and Berch).

Zwitterionic Surfactants

Zwitterionic surfactants can be thought of as a subset of the amphotericsurfactants and can include an anionic charge. Zwitterionic surfactantscan be broadly described as derivatives of secondary and tertiaryamines, derivatives of heterocyclic secondary and tertiary amines, orderivatives of quaternary ammonium, quaternary phosphonium or tertiarysulfonium compounds. Typically, a zwitterionic surfactant includes apositive charged quaternary ammonium or, in some cases, a sulfonium orphosphonium ion; a negative charged carboxyl group; and an alkyl group.Zwitterionics generally contain cationic and anionic groups which ionizeto a nearly equal degree in the isoelectric region of the molecule andwhich can develop strong “inner-salt” attraction betweenpositive-negative charge centers. Examples of such zwitterionicsynthetic surfactants include derivatives of aliphatic quaternaryammonium, phosphonium, and sulfonium compounds, in which the aliphaticradicals can be straight chain or branched, and wherein one of thealiphatic substituents contains from 8 to 18 carbon atoms and onecontains an anionic water solubilizing group, e.g., carboxy, sulfonate,sulfate, phosphate, or phosphonate. Betaine and sultaine surfactants areexemplary zwitterionic surfactants for use herein.

A general formula for these compounds is:

wherein R¹ contains an alkyl, alkenyl, or hydroxyalkyl radical of from 8to 18 carbon atoms having from 0 to 10 ethylene oxide moieties and from0 to 1 glyceryl moiety; Y is selected from the group consisting ofnitrogen, phosphorus, and sulfur atoms; R² is an alkyl or monohydroxyalkyl group containing 1 to 3 carbon atoms; x is 1 when Y is a sulfuratom and 2 when Y is a nitrogen or phosphorus atom, R³ is an alkylene orhydroxy alkylene or hydroxy alkylene of from 1 to 4 carbon atoms and Zis a radical selected from the group consisting of carboxylate,sulfonate, sulfate, phosphonate, and phosphate groups.

Examples of zwitterionic surfactants having the structures listed aboveinclude:4-[N,N-di(2-hydroxyethyl)-N-octadecylammonio]-butane-1-carboxylate;5-[S-3-hydroxypropyl-S-hexadecylsulfonio]-3-hydroxypentane-1-sulfate;3-[P,P-diethyl-P-3,6,9-trioxatetracosanephosphonio]-2-hydroxypropane-1-phosphate;3-[N,N-dipropyl-N-3-dodecoxy-2-hydroxypropyl-ammonio]-propane-1-phosphonate;3-(N,N-dimethyl-N-hexadecylammonio)-propane-1-sulfonate;3-(N,N-dimethyl-N-hexadecylammonio)-2-hydroxy-propane-1-sulfonate;4-[N,N-di(2(2-hydroxyethyl)-N(2-hydroxydodecyl)ammonio]-butane-1-carboxylate;3-[S-ethyl-S-(3-dodecoxy-2-hydroxypropyl)sulfonio]-propane-1-phosphate;3-[P,P-dimethyl-P-dodecylphosphonio]-propane-1-phosphonate; andS[N,N-di(3-hydroxypropyl)-N-hexadecylammonio]-2-hydroxy-pentane-1-sulfate.The alkyl groups contained in said detergent surfactants can be straightor branched and saturated or unsaturated.

The zwitterionic surfactant suitable for use in the present compositionsincludes a betaine of the general structure:

These surfactant betaines typically do not exhibit strong cationic oranionic characters at pH extremes nor do they show reduced watersolubility in their isoelectric range. Unlike “external” quaternaryammonium salts, betaines are compatible with anionics. Examples ofsuitable betaines include coconut acylamidopropyldimethyl betaine;hexadecyl dimethyl betaine; C₁₂₋₁₄ acylamidopropylbetaine; C₈₋₁₄acylamidohexyldiethyl betaine; 4-C₁₄₋₁₆acylmethylamidodiethylammonio-1-carboxybutane; C₁₆₋₁₈acylamidodimethylbetaine; C₁₂₋₁₆ acylamidopentanediethylbetaine; andC₁₂₋₁₆ acylmethylamidodimethylbetaine.

Sultaines useful in the present invention include those compounds havingthe formula (R(R¹)₂N⁺R²SO³⁻, in which R is a C₆-C₁₈ hydrocarbyl group,each R¹ is typically independently C₁-C₃ alkyl, e.g. methyl, and R² is aC₁-C₆ hydrocarbyl group, e.g. a C₁-C₃ alkylene or hydroxyalkylene group.

A typical listing of zwitterionic classes, and species of thesesurfactants, is given in U.S. Pat. No. 3,929,678 issued to Laughlin andHeuring on Dec. 30, 1975. Further examples are given in “Surface ActiveAgents and Detergents” (Vol. I and II by Schwartz, Perry and Berch).

In an embodiment, the compositions of the present invention include abetaine. For example, the compositions can include cocoamidopropylbetaine.

Other Additional Ingredients

In some embodiments, the compositions of the present invention caninclude other additional ingredients. Additional ingredients suitablefor use with the compositions of the present invention include, but arenot limited to, acidulants, stabilizing agents, e.g., chelating agentsor sequestrants, buffers, detergents, wetting agents, defoaming agents,thickeners, foaming agents, solidification agents, aesthetic enhancingagents (i.e., colorants, odorants, or perfumes) and other cleaningagents. These additional ingredients can be preformulated with thecompositions of the invention or added to the system before, after, orsubstantially simultaneously with the addition of the compositions ofthe present invention. Additionally, the compositions can be used inconjunction with one or more conventional cleaning agents, e.g., analkaline detergent.

Acidulants

In some embodiments, the compositions of the present invention includean acidulant. The acidulant can act as a catalyst for conversion ofcarboxylic acid to peroxycarboxylic acid. The acidulant can be effectiveto form a concentrate composition with pH of about 0.01 to about 7 orless, a pH of about 1 to about 6, or a pH of about 2 to about 5. Theacidulant can be effective to form a use composition with pH of about 4to about 9, about 5 to about 8, about 5.5 to about 7.5. In someembodiments, an acidulant can be used to lower the pH of an alkalinecleaning solution to a pH of about 10, about 10 or less, about 9, about9 or less, about 8, about 8 or less, about 7, about 7 or less, about 6,or about 6 or less. In an embodiment, the acidulant includes aninorganic acid. Suitable inorganic acids include, but are not limitedto, sulfuric acid, sodium bisulfate, phosphoric acid, nitric acid,hydrochloric acid. In some embodiments, the acidulant includes anorganic acid. Suitable organic acids include, but are not limited to,methane sulfonic acid, ethane sulfonic acid, propane sulfonic acid,butane sulfonic acid, xylene sulfonic acid, benzene sulfonic acid,linear alkyl benzene sulphonic acid, cumene sulfonic acid, xylenesulfonic acid, formic acid, acetic acid, glycolic acid, mono, di, ortri-halocarboyxlic acids, picolinic acid, dipicolinic acid, and mixturesthereof. In some embodiments, the compositions of the present inventionare free or substantially free of a phosphorous based acid.

In some embodiments, the acidulant selected can also function as astabilizing agent. Thus, the compositions of the present invention canbe substantially free of an additional stabilizing agent.

In certain embodiments, the present composition includes about 0.5 toabout 80 wt-% acidulant, about 1 to about 50 wt %, about 5 to about 30wt-% acidulant, or about 7 to about 14 wt-% acidulant. It is to beunderstood that all values and ranges between these values and rangesare encompassed by the compositions of the present invention.

Stabilizing Agents

In some embodiments, the compositions of the present invention includeone or more stabilizing agents. The stabilizing agents can be used, forexample, to stabilize the peracid and hydrogen peroxide and prevent thepremature oxidation of this constituent within the composition of theinvention.

In some embodiments, an acidic stabilizing agent can be used. Thus, insome embodiments, the compositions of the present invention can besubstantially free of an additional acidulant.

Suitable stabilizing agents include, for example, chelating agents orsequestrants. Suitable sequestrants include, but are not limited to,organic chelating compounds that sequester metal ions in solution,particularly transition metal ions. Such sequestrants include organicamino- or hydroxy-polyphosphonic acid complexing agents (either in acidor soluble salt forms), carboxylic acids (e.g., polymericpolycarboxylate), hydroxycarboxylic acids, aminocarboxylic acids, orheterocyclic carboxylic acids, e.g., pyridine-2,6-dicarboxylic acid(dipicolinic acid).

In some embodiments, the compositions of the present invention includedipicolinic acid as a stabilizing agent. Compositions includingdipicolinic acid can be formulated to be free or substantially free ofphosphorous. It has also been observed that the inclusion of dipicolinicacid in a composition of the present invention aids in achieving thephase stability of the compositions, compared to other conventionalstabilizing agents, e.g., 1-hydroxy ethylidene-1,1-diphosphonic acid(CH₃C(PO₃H₂)₂OH) (HEDP).

When nonionic surfactants having an ethylene oxide (EO) hydrophilicblock are used in compositions of the invention and/or when certainother anionic and/or certain other amine oxide surfactants, someformulations may phase separate or suffer from visible cloudiness orhaziness. In the event of such phase separation or visible cloudiness, asmall amount of a hydrotrope, such as sodium cumene sulfonate (“SCS”)may be added to the composition. Up to about 10 weight percent, up toabout 8 weight percent, up to about 5 weight percent, and up to about 3weight percent hydrotrope may be added to clear and/or eliminate phaseseparation of the formulation.

In other embodiments, the sequestrant can be or include phosphonic acidor phosphonate salt. Suitable phosphonic acids and phosphonate saltsinclude HEDP; ethylenediamine tetrakis methylenephosphonic acid (EDTMP);diethylenetriamine pentakis methylenephosphonic acid (DTPMP);cyclohexane-1,2-tetramethylene phosphonic acid; amino[tri(methylenephosphonic acid)]; (ethylene diamine[tetra methylene-phosphonic acid)];2-phosphene butane-1,2,4-tricarboxylic acid; or salts thereof, such asthe alkali metal salts, ammonium salts, or alkyloyl amine salts, such asmono, di, or tetra-ethanolamine salts; picolinic, dipicolinic acid ormixtures thereof. In some embodiments, organic phosphonates, e.g, HEDPare included in the compositions of the present invention.

Commercially available food additive chelating agents includephosphonates sold under the trade name DEQUEST® including, for example,1-hydroxyethylidene-1,1-diphosphonic acid, available from MonsantoIndustrial Chemicals Co., St. Louis, Mo., as DEQUEST® 2010;amino(tri(methylenephosphonic acid)), (N[CH₂PO₃H₂]₃), available fromMonsanto as DEQUEST® 2000; ethylenediamine[tetra(methylenephosphonicacid)] available from Monsanto as DEQUEST® 2041; and2-phosphonobutane-1,2,4-tricarboxylic acid available from Mobay ChemicalCorporation, Inorganic Chemicals Division, Pittsburgh, Pa., as BayhibitAM.

The sequestrant can be or include aminocarboxylic acid type sequestrant.Suitable aminocarboxylic acid type sequestrants include the acids oralkali metal salts thereof, e.g., amino acetates and salts thereof.Suitable aminocarboxylates include N-hydroxyethylaminodiacetic acid;hydroxyethylenediaminetetraacetic acid, nitrilotriacetic acid (NTA);ethylenediaminetetraacetic acid (EDTA);N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA);diethylenetriaminepentaacetic acid (DTPA); and alanine-N,N-diaceticacid; and the like; and mixtures thereof.

The sequestrant can be or include a polycarboxylate. Suitablepolycarboxylates include, for example, polyacrylic acid, maleic/olefincopolymer, acrylic/maleic copolymer, polymethacrylic acid, acrylicacid-methacrylic acid copolymers, hydrolyzed polyacrylamide, hydrolyzedpolymethacrylamide, hydrolyzed polyamide-methacrylamide copolymers,hydrolyzed polyacrylonitrile, hydrolyzed polymethacrylonitrile,hydrolyzed acrylonitrile-methacrylonitrile copolymers, polymaleic acid,polyfumaric acid, copolymers of acrylic and itaconic acid, phosphinopolycarboxylate, acid or salt forms thereof, mixtures thereof, and thelike.

In certain embodiments, the present composition includes about 0.01 toabout 10 wt-% stabilizing agent, about 0.4 to about 4 wt-% stabilizingagent, about 0.6 to about 3 wt-% stabilizing agent, about 1 to about 2wt-% stabilizing agent. It is to be understood that all values andranges within these values and ranges are encompassed by the presentinvention.

Wetting or Defoaming Agents

Also useful in the compositions of the invention are wetting anddefoaming agents. Wetting agents function to increase the surfacecontact or penetration activity of the antimicrobial composition of theinvention. Wetting agents which can be used in the composition of theinvention include any of those constituents known within the art toraise the surface activity of the composition of the invention.

Generally, defoamers which can be used in accordance with the inventioninclude silica and silicones; aliphatic acids or esters; alcohols;sulfates or sulfonates; amines or amides; halogenated compounds such asfluorochlorohydrocarbons; vegetable oils, waxes, mineral oils as well astheir sulfonated or sulfated derivatives; fatty acids and/or their soapssuch as alkali, alkaline earth metal soaps; and phosphates and phosphateesters such as alkyl and alkaline diphosphates, and tributyl phosphatesamong others; and mixtures thereof.

In some embodiments, the compositions of the present invention caninclude antifoaming agents or defoamers which are of food grade qualitygiven the application of the method of the invention. To this end, oneof the more effective antifoaming agents includes silicones. Siliconessuch as dimethyl silicone, glycol polysiloxane, methylphenolpolysiloxane, trialkyl or tetralkyl silanes, hydrophobic silicadefoamers and mixtures thereof can all be used in defoamingapplications. Commercial defoamers commonly available include siliconessuch as Ardefoam® from Armour Industrial Chemical Company which is asilicone bound in an organic emulsion; Foam Kill® or Kresseo® availablefrom Krusable Chemical Company which are silicone and non-silicone typedefoamers as well as silicone esters; and Anti-Foam A® and DC-200 fromDow Corning Corporation which are both food grade type silicones amongothers. These defoamers can be present at a concentration range fromabout 0.01 wt-% to 20 wt-%, from about 0.01 wt-% to 5 wt-%, or fromabout 0.01 wt-% to about 1 wt-%.

In some embodiments, the compositions of the present invention caninclude antifoaming agents or defoaming agents which are based onalcohol alkoxylates that are stable in acid environments and areoxidatively stable. To this end one of the more effective antifoamingagents are the alcohol alkoxylates having an alcohol chain length ofabout C8-12, and more specifically C9-11, and having poly-propyleneoxide alkoxylate in whole or part of the alkylene oxide portion.Commercial defoamers commonly available of this type include alkoxylatessuch as the BASF Degressal's; especially Degressal SD20.

Thickening or Gelling Agents

The compositions of the present invention can include any of a varietyof known thickeners. Suitable thickeners include natural gums such asxanthan gum, guar gum, or other gums from plant mucilage; polysaccharidebased thickeners, such as alginates, starches, and cellulosic polymers(e.g., carboxymethyl cellulose); polyacrylates thickeners; andhydrocolloid thickeners, such as pectin. Other suitable thickenersinclude synthetic materials, for example, polyacrylates,polyacrylamides, polyalkylene glycols and derivatives includingpolyethylene glycols or polypropylene glycols, polyvinyl derivativessuch as polyvinyl alcohols and/or polyvinyl acetates, or co-polymersthereof, and other polyvinyl derivatives, and mixtures thereof.Polycarboxylic acids are also useful as thickening agents incompositions of the invention. ACUS OL® 445 is a partially neutralized,liquid detergent polymer. Other polyacrylic acids of molecular weight4500 (CRITERION 2005) and 8000 (CRITERION 2108) can be purchased fromKemira Chemicals, Kennesaw, Ga. Other thickening agents include, but arenot limited to, Soakalan CP5 available from BASF, Coatex DE185, and IsolDispersant HN44. In some embodiments, the thickener included is nonoxidizable and storage stable under the pH conditions of the invention.In an embodiment, the thickener does not leave contaminating residue onthe surface of an object. For example, the thickeners or gelling agentscan be compatible with food or other sensitive products in contactareas. Generally, the concentration of thickener employed in the presentcompositions or methods will be dictated by the desired viscosity withinthe final composition. However, as a general guideline, the viscosity ofthickener within the present composition ranges from about 0.1 wt-% toabout 5 wt-%, from about 0.1 wt-% to about 1.0 wt-%, or from about 0.1wt-% to about 0.5 wt-%.

Solidification Agents

The present compositions can include a solidification agent, which canparticipate in maintaining the compositions in a solid form. In someembodiments, the solidification agent can form and/or maintain thecomposition as a solid. In other embodiments, the solidification agentcan solidify the composition without unacceptably detracting from theeventual release of the sulfonated peroxycarboxylic acid. Thesolidification agent can include, for example, an organic or inorganicsolid compound having a neutral inert character or making a functional,stabilizing or detersive contribution to the present composition.Suitable solidification agents include solid or paste polyethyleneglycols (PEG), solid or paste polypropylene glycols, solid EO/PO blockcopolymer, amide, urea (also known as carbamide), nonionic surfactant(which can be employed with a coupler), anionic surfactant, starch thathas been made water-soluble (e.g., through an acid or alkaline treatmentprocess), cellulose that has been made water-soluble, inorganic agent,poly(maleic anhydride/methyl vinyl ether), polymethacrylic acid, othergenerally functional or inert materials with high melting points,mixtures thereof, and the like;

Suitable glycol solidification agents include a solid polyethyleneglycol or a solid polypropylene glycol, which can, for example, havemolecular weight of about 1,400 to about 30,000. In certain embodiments,the solidification agent includes or is solid PEG, for example PEG 1500up to PEG 20,000. In certain embodiments, the PEG includes PEG 1450, PEG3350, PEG 4500, PEG 8000, PEG 20,000, and the like. Suitable solidpolyethylene glycols are commercially available from Union Carbide underthe tradename CARBOWAX.

Suitable amide solidification agents include stearic monoethanolamide,lauric diethanolamide, stearic diethanolamide, stearic monoethanolamide, cocodiethylene amide, an alkylamide, mixtures thereof, and thelike. In an embodiment, the present composition can include glycol(e.g., PEG) and amide.

Suitable nonionic surfactant solidification agents include nonylphenolethoxylate, linear alkyl alcohol ethoxylate, ethylene oxide/propyleneoxide block copolymer, mixtures thereof, or the like. Suitable ethyleneoxide/propylene oxide block copolymers include those sold under thePluronic tradename (e.g., Pluronic 108 and Pluronic F68) andcommercially available from BASF Corporation. In some embodiments, thenonionic surfactant can be selected to be solid at room temperature orthe temperature at which the composition will be stored or used. Inother embodiments, the nonionic surfactant can be selected to havereduced aqueous solubility in combination with the coupling agent.Suitable couplers that can be employed with the nonionic surfactantsolidification agent include propylene glycol, polyethylene glycol,mixtures thereof, or the like.

Suitable anionic surfactant solidification agents include linear alkylbenzene sulfonate, alcohol sulfate, alcohol ether sulfate, alpha olefinsulfonate, mixtures thereof, and the like. In an embodiment, the anionicsurfactant solidification agent is or includes linear alkyl benzenesulfonate. In an embodiment, the anionic surfactant can be selected tobe solid at room temperature or the temperature at which the compositionwill be stored or used.

Suitable inorganic solidification agents include phosphate salt (e.g.,alkali metal phosphate), sulfate salt (e.g., magnesium sulfate, sodiumsulfate or sodium bisulfate), acetate salt (e.g., anhydrous sodiumacetate), Borates (e.g., sodium borate), Silicates (e.g., theprecipitated or fumed forms (e.g., Sipernat 50® available from Degussa),carbonate salt (e.g., calcium carbonate or carbonate hydrate), otherknown hydratable compounds, mixtures thereof, and the like. In anembodiment, the inorganic solidification agent can include organicphosphonate compound and carbonate salt, such as an E-Form composition.

In some embodiments, the compositions of the present invention caninclude any agent or combination of agents that provide a requisitedegree of solidification and aqueous solubility can be included in thepresent compositions. In other embodiments, increasing the concentrationof the solidification agent in the present composition can tend toincrease the hardness of the composition. In yet other embodiments,decreasing the concentration of solidification agent can tend to loosenor soften the concentrate composition.

In some embodiments, the solidification agent can include any organic orinorganic compound that imparts a solid character to and/or controls thesoluble character of the present composition, for example, when placedin an aqueous environment. For example, a solidifying agent can providecontrolled dispensing if it has greater aqueous solubility compared toother ingredients in the composition. Urea can be one suchsolidification agent. By way of further example, for systems that canbenefit from less aqueous solubility or a slower rate of dissolution, anorganic nonionic or amide hardening agent may be appropriate.

In some embodiments, the compositions of the present invention caninclude a solidification agent that provides for convenient processingor manufacture of the present composition. For example, thesolidification agent can be selected to form a composition that canharden to a solid form under ambient temperatures of about 30 to about50° C. after mixing ceases and the mixture is dispensed from the mixingsystem, within about 1 minute to about 3 hours, or about 2 minutes toabout 2 hours, or about 5 minutes to about 1 hour.

The compositions of the present invention can include solidificationagent at any effective amount. The amount of solidification agentincluded in the present composition can vary according to the type ofcomposition, the ingredients of the composition, the intended use of thecomposition, the quantity of dispensing solution applied to the solidcomposition over time during use, the temperature of the dispensingsolution, the hardness of the dispensing solution, the physical size ofthe solid composition, the concentration of the other ingredients, theconcentration of the cleaning agent in the composition, and other likefactors. Suitable amounts can include about 1 to about 99 wt-%, about1.5 to about 85 wt-%, about 2 to about 80 wt-%, about 10 to about 45wt-%, about 15% to about 40 wt-%, about 20% to about 30 wt-%, about 30%to about 70%, about 40% to about 60%, up to about 50 wt-%, about 40% toabout 50%

Carriers

In some embodiments, the compositions of the present invention include acarrier. The carrier provides a medium which dissolves, suspends, orcarries the other components of the composition. For example, thecarrier can provide a medium for solubilization, suspension, orproduction of a sulfonated peroxycarboxylic acid and for forming anequilibrium mixture. The carrier can also function to deliver and wetthe composition of the invention on an object. To this end, the carriercan contain any component or components that can facilitate thesefunctions.

In some embodiments, the carrier includes primarily water which canpromote solubility and work as a medium for reaction and equilibrium.The carrier can include or be primarily an organic solvent, such assimple alkyl alcohols, e.g., ethanol, isopropanol, n-propanol, benzylalcohol, and the like. Polyols are also useful carriers, includingglycerol, sorbitol, and the like.

Suitable carriers include glycol ethers. Suitable glycol ethers includediethylene glycol n-butyl ether, diethylene glycol n-propyl ether,diethylene glycol ethyl ether, diethylene glycol methyl ether,diethylene glycol t-butyl ether, dipropylene glycol n-butyl ether,dipropylene glycol methyl ether, dipropylene glycol ethyl ether,dipropylene glycol propyl ether, dipropylene glycol tert-butyl ether,ethylene glycol butyl ether, ethylene glycol propyl ether, ethyleneglycol ethyl ether, ethylene glycol methyl ether, ethylene glycol methylether acetate, propylene glycol n-butyl ether, propylene glycol ethylether, propylene glycol methyl ether, propylene glycol n-propyl ether,tripropylene glycol methyl ether and tripropylene glycol n-butyl ether,ethylene glycol phenyl ether (commercially available as DOWANOL EPH™from Dow Chemical Co.), propylene glycol phenyl ether (commerciallyavailable as DOWANOL PPH™ from Dow Chemical Co.), and the like, ormixtures thereof. Additional suitable commercially available glycolethers (all of which are available from Union Carbide Corp.) includeButoxyethyl PROPASOL™, Butyl CARBITOL™ acetate, Butyl CARBITOL™, ButylCELLOSOLVE™ acetate, Butyl CELLOSOLVE™, Butyl DIPROPASOL™, ButylPROPASOL™, CARBITOL™ PM-600, CARBITOL™ Low Gravity, CELLOSOLVE™ acetate,CELLOSOLVE™, Ester EEP™, FILMER IBT™, Hexyl CARBITOL™, HexylCELLOSOLVE™, Methyl CARBITOL™, Methyl CELLOSOLVE™ acetate, MethylCELLOSOLVE™, Methyl DIPROPASOL™, Methyl PROPASOL™ acetate, MethylPROPASOL™, Propyl CARBITOL™, Propyl CELLOSOLVE™, Propyl DIPROPASOL™ andPropyl PROPASOL™.

In some embodiments, the carrier makes up a large portion of thecomposition of the invention and may be the balance of the compositionapart from the sulfonated peroxycarboxylic acid, oxidizing agent,additional ingredients, and the like. The carrier concentration and typewill depend upon the nature of the composition as a whole, theenvironmental storage, and method of application including concentrationof the sulfonated peroxycarboxylic acid, among other factors. Notablythe carrier should be chosen and used at a concentration which does notinhibit the efficacy of the sulfonated peroxycarboxylic acid in thecomposition of the invention for the intended use, e.g., bleaching,sanitizing, disinfecting.

In certain embodiments, the present composition includes about 5 toabout 90 wt-% carrier, about 10 to about 80 wt % carrier, about 20 toabout 60 wt % carrier, or about 30 to about 40 wt % carrier. It is to beunderstood that all values and ranges between these values and rangesare encompassed by the present invention.

Additional Function Ingredients

In some embodiments, the compositions include additional functionalingredients. Additional functional ingredients suitable for inclusion inthe compositions include, but are not limited to, optical brighteners,soil antiredeposition agents, antifoam agents, low foaming surfactants,defoaming surfactants, pigments and dyes, softening agents, anti-staticagents, anti-wrinkling agents, dye transfer inhibition/color protectionagents, odor removal/odor capturing agents, soil shielding/soilreleasing agents, ultraviolet light protection agents, fragrances,sanitizing agents, disinfecting agents, water repellency agents, insectrepellency agents, anti-pilling agents, souring agents, mildew removingagents, allergicide agents, and mixtures thereof. In some embodiments,the additional functional ingredient or ingredients is formulated in thecompositions. In other embodiments, the additional functional ingredientor ingredients is added separately during a cleaning process.

Color Stabilizing Agent

In some embodiments, the compositions optionally include a colorstabilizing agent. A color stabilizing agent can be any component thatis included to inhibit discoloration or browning of the composition. Insome embodiments, a color stabilizing agent may be included in thecompositions at an amount of from about 0.01 to about 5 wt %, from about0.05 to about 3 wt %, and from about 0.10 to about 2 wt %.

Optical Brighteners

In some embodiments, the compositions optionally include an opticalbrightener. Brighteners are added to laundry detergents to replacewhitening agents removed during washing and to make the clothes appearcleaner. Optical brighteners may include dyes that absorb light in theultraviolet and violet region (usually 340-370 nm) of theelectromagnetic spectrum, and re-emit light in the blue region(typically 420-470 nm). These additives are often used to enhance theappearance of the color of a fabric, causing a perceived “whitening”effect, making materials look less yellow by increasing the overallamount of blue light reflected. In some embodiments, optical brightenerssuitable for inclusion in the compositions, include, but are not limitedto, triazine-stilbenes (di-, tetra- or hexa-sulfonated), coumarins,imidazolines, diazoles, triazoles, benzoxazolines, biphenyl-stilbenes,and mixtures thereof. One or more optical brighteners may be used in thecompositions. In some embodiments, optical brighteners are included inthe compositions at an amount of from about 0.1 to about 5 wt %, fromabout 0.15 to about 3 wt %, or from about 0.2 to about 2 wt %. Examplesof commercially available optical brighteners suitable for use in thecompositions include, but are not limited to, DMS-X and CBS-X, adistyryl biphenyl derivative, both available from Vesta-Intracon BV.

Soil Antiredeposition Agents

In some embodiments, the compositions may optionally includeantiredeposition agents. Without wishing to be bound by any particulartheory, it is thought that antiredeposition agents aid in preventingloosened soil from redepositing onto cleaned fabrics. Antiredepositionagents may be made from complex cellulosic materials such ascarboxymethylcellulose (CMC), or synthetic materials such aspolyethylene glycol and polyacrylates. In other embodiments,polyphosphate builders may be included as an antiredeposition agent.

Use Compositions

The compositions of the present invention include concentratecompositions and use compositions. For example, a concentratecomposition can be diluted, for example with water, to form a usecomposition. In an embodiment, a concentrate composition can be dilutedto a use solution before applying to an object. For reasons ofeconomics, the concentrate can be marketed and an end user can dilutethe concentrate with water or an aqueous diluent to a use solution.

The level of active components in the concentrate composition isdependent on the intended dilution factor and the desired activity ofthe sulfonated peroxycarboxylic acid compound. Generally, a dilution ofabout 1 fluid ounce to about 10 gallons of water to about 10 fluidounces to about 1 gallon of water is used for aqueous compositions ofthe present invention. In some embodiments, higher use dilutions can beemployed if elevated use temperature (greater than 25° C.) or extendedexposure time (greater than 30 seconds) can be employed. In the typicaluse locus, the concentrate is diluted with a major proportion of waterusing commonly available tap or service water mixing the materials at adilution ratio of about 3 to about 40 ounces of concentrate per 100gallons of water.

In some embodiments, when used in a laundry application, theconcentrated compositions can be diluted at a dilution ratio of about0.1 g/L to about 100 g/L concentrate to diluent, about 0.5 g/L to about10.0 g/L concentrate to diluent, about 1.0 g/L to about 4.0 g/Lconcentrate to diluent, or about 1.0 g/L to about 2.0 g/L concentrate todiluent.

In other embodiments, a use composition can include about 0.01 to about10 wt-% of a concentrate composition and about 90 to about 99.99 wt-%diluent; or about 0.1 to about 1 wt-% of a concentrate composition andabout 99 to about 99.9 wt-% diluent.

Amounts of an ingredient in a use composition can be calculated from theamounts listed above for concentrate compositions and these dilutionfactors. In some embodiments, for example when used in a laundryapplication, the concentrated compositions of the present invention arediluted such that the sulfopercarboxylic acid is present at from about20 ppm to about 80 ppm. In other embodiments, the concentratedcompositions of the present invention are diluted such that thesulfopercarboxylic acid is present at about 20 ppm, about 40 ppm, about60 ppm, about 80 ppm, about 500 ppm, about 1000 ppm, or about 10,000 toabout 20,000 ppm. It is to be understood that all values and rangesbetween these values and ranges are encompassed by the presentinvention.

Methods Employing the Sulfoperoxycarboxylic Acid Compounds andCompositions

In some aspects, the present invention includes methods of using thesulfoperoxycarboxylic acid compounds and compositions of the presentinvention. In some embodiments, these methods employ the antimicrobialand/or bleaching activity of the sulfoperoxycarboxylic acid. Forexample, the invention includes a method for reducing a microbialpopulation, a method for reducing the population of a microorganism onskin, a method for treating a disease of skin, a method for reducing anodor, and/or a method for bleaching. These methods can operate on anarticle, surface, in a body or stream of water or a gas, or the like, bycontacting the article, surface, body, or stream with asulfoperoxycarboxylic acid compound or composition of the invention.Contacting can include any of numerous methods for applying a compoundor composition of the invention, such as spraying the compounds orcompositions, immersing the article in the compounds or compositions,foam or gel treating the article with the compounds or composition, or acombination thereof.

In some aspects, a composition of the present invention includes anamount of sulfoperoxycarboxylic acid of the present invention effectivefor killing one or more of the food-borne pathogenic bacteria associatedwith a food product, including, but not limited to, Salmonellatyphimurium, Salmonella javiana, Campylobacter jejuni, Listeriamonocytogenes, and Escherichia coli O157:H7, yeast, and mold. In someembodiments, the compositions of the present invention include an amountof sulfoperoxycarboxylic acid effective for killing one or more of thepathogenic bacteria associated with a health care surfaces andenvironments including, but not limited to, Salmonella typhimurium,Staphylococcus aureus, methicillin resistant Staphylococcus aureus,Salmonella choleraesurus, Pseudomonas aeruginosa, Escherichia coli,mycobacteria, yeast, and mold. The compounds and compositions of thepresent invention have activity against a wide variety of microorganismssuch as Gram positive (for example, Listeria monocytogenes orStaphylococcus aureus) and Gram negative (for example, Escherichia colior Pseudomonas aeruginosa) bacteria, yeast, molds, bacterial spores,viruses, etc. The compounds and compositions of the present invention,as described above, have activity against a wide variety of humanpathogens. The present compounds and compositions can kill a widevariety of microorganisms on a food processing surface, on the surfaceof a food product, in water used for washing or processing of foodproduct, on a health care surface, or in a health care environment.

The compounds of the invention can be used for a variety of domestic orindustrial applications, e.g., to reduce microbial or viral populationson a surface or object or in a body or stream of water. The compoundscan be applied in a variety of areas including kitchens, bathrooms,factories, hospitals, dental offices and food plants, and can be appliedto a variety of hard or soft surfaces having smooth, irregular or poroustopography. Suitable hard surfaces include, for example, architecturalsurfaces (e.g., floors, walls, windows, sinks, tables, counters andsigns); eating utensils; hard-surface medical or surgical instrumentsand devices; and hard-surface packaging. Such hard surfaces can be madefrom a variety of materials including, for example, ceramic, metal,glass, wood or hard plastic. Suitable soft surfaces include, for examplepaper; filter media; hospital and surgical linens and garments;soft-surface medical or surgical instruments and devices; andsoft-surface packaging. Such soft surfaces can be made from a variety ofmaterials including, for example, paper, fiber, woven or nonwovenfabric, soft plastics and elastomers. The compounds of the invention canalso be applied to soft surfaces such as food and skin (e.g., a hand).The present compounds can be employed as a foaming or nonfoamingenvironmental sanitizer or disinfectant.

The compounds and compositions of the invention can be included inproducts such as sterilants, sanitizers, disinfectants, preservatives,deodorizers, antiseptics, fungicides, germicides, sporicides, virucides,detergents, bleaches, hard surface cleaners, hand soaps, waterless handsanitizers, and pre- or post-surgical scrubs.

The compounds can also be used in veterinary products such as mammalianskin treatments or in products for sanitizing or disinfecting animalenclosures, pens, watering stations, and veterinary treatment areas suchas inspection tables and operation rooms. The present compounds can beemployed in an antimicrobial foot bath for livestock or people. Thecompounds of the present invention can also be employed as anantimicrobial teat dip.

In some aspects, the compounds of the present invention can be employedfor reducing the population of pathogenic microorganisms, such aspathogens of humans, animals, and the like. The compounds exhibitactivity against pathogens including fungi, molds, bacteria, spores, andviruses, for example, S. aureus, E. coli, Streptococci, Legionella,Pseudomonas aeruginosa, mycobacteria, tuberculosis, phages, or the like.Such pathogens can cause a variety of diseases and disorders, includingmastitis or other mammalian milking diseases, tuberculosis, and thelike. The compounds of the present invention can reduce the populationof microorganisms on skin or other external or mucosal surfaces of ananimal. In addition, the present compounds can kill pathogenicmicroorganisms that spread through transfer by water, air, or a surfacesubstrate. The compounds need only be applied to the skin, otherexternal or mucosal surfaces of an animal water, air, or surface.

In some embodiments, the compounds and compositions of the presentinvention can be used to reduce the population of prions on a surface.Prions are proteinaceous infections particles free of nucleic acid.Prions are known to cause several brain diseases including kuru,Creutzfeldt-Jakob disease, Gerstmann-Straussler-Scheinker disease, andfatal familial insomnia in humans; scrapie in sheep; bovine spongiformencephalopathy (Mad Cow Disease) in cattle; transmissible minkencephalopathy in mink; chronic wasting disease in deer and elk; andfeline spongiform encephalopathy in cats. These diseases lead tosymptoms including dementia, ataxia, behavioral disturbances, dizziness,involuntary movement, and death. Prions can be transmitted by exposureto infected tissue and brain tissue, spinal cord tissue, pituitarytissue, and eye tissue in particular. In some embodiments, the compoundsand compositions of the present invention can be used to reduce apopulation of prions according to a method as described in U.S. Pat. No.7,470,655, the entire contents of which are hereby incorporated byreference.

The antimicrobial compounds can also be used on foods and plant speciesto reduce surface microbial populations; used at manufacturing orprocessing sites handling such foods and plant species; or used to treatprocess waters around such sites. For example, the compounds can be usedon food transport lines (e.g., as belt sprays); boot and hand-washdip-pans; food storage facilities; anti-spoilage air circulationsystems; refrigeration and cooler equipment; beverage chillers andwarmers, blanchers, cutting boards, third sink areas, and meat chillersor scalding devices. The compounds of the invention can be used to treatproduce transport waters such as those found in flumes, pipe transports,cutters, slicers, blanchers, retort systems, washers, and the like.Particular foodstuffs that can be treated with compounds of theinvention include eggs, meats, seeds, leaves, fruits and vegetables.Particular plant surfaces include both harvested and growing leaves,roots, seeds, skins or shells, stems, stalks, tubers, corms, fruit, andthe like. The compounds may also be used to treat animal carcasses toreduce both pathogenic and non-pathogenic microbial levels.

The antimicrobial compounds can also be used to treat waste water whereboth its antimicrobial function and its oxidant properties can beutilized. Aside from the microbial issues surrounding waste water, it isoften rich in malodorous compounds of reduced sulfur, nitrogen orphosphorous. A strong oxidant such as the present invention convertsthese compounds efficiently to their odor free derivatives e.g. thesulfates, phosphates and amine oxides. These same properties are veryuseful in the pulp and paper industry where the property of bleaching isalso of great utility.

In some aspects, the compounds of the present invention can be employedfor epoxidations. The polymer industry is a major consumer of peracids,especially peroxyacetic acid but the typical equilibrium peroxyaceticacid also includes some strong acid residues which are problematic forthe epoxide derivatives. A stable peracid isolate is thereforepotentially of great utility in this industry.

In some aspects, the compounds and compositions of the present inventionare useful in the cleaning or sanitizing of containers, processingfacilities, or equipment in the food service or food processingindustries. The compounds and compositions have particular value for useon food packaging materials and equipment, and especially for cold orhot aseptic packaging. Examples of process facilities in which thecompound of the invention can be employed include a milk line dairy, acontinuous brewing system, food processing lines such as pumpable foodsystems and beverage lines, etc. Food service wares can be disinfectedwith the compound of the invention. For example, the compounds can alsobe used on or in ware wash machines, low temperature ware wash machines,dishware, bottle washers, bottle chillers, warmers, third sink washers,cutting areas (e.g., water knives, slicers, cutters and saws) and eggwashers. Particular treatable surfaces include packaging such ascartons, bottles, films and resins; dish ware such as glasses, plates,utensils, pots and pans; ware wash and low temperature ware washmachines; exposed food preparation area surfaces such as sinks,counters, tables, floors and walls; processing equipment such as tanks,vats, lines, pumps and hoses (e.g., dairy processing equipment forprocessing milk, cheese, ice cream and other dairy products); andtransportation vehicles. Containers include glass bottles, PVC orpolyolefin film sacks, cans, polyester, PEN or PET bottles of variousvolumes (100 ml to 2 liter, etc.), one gallon milk containers, paperboard juice or milk containers, etc.

The compounds and compositions can also be used on or in otherindustrial equipment and in other industrial process streams such asheaters, cooling towers, boilers, retort waters, rinse waters, asepticpackaging wash waters, and the like. The compounds can be used to treatmicrobes and odors in recreational waters such as in pools, spas,recreational flumes and water slides, fountains, and the like.

A filter containing the compound can reduce the population ofmicroorganisms in air and liquids. Such a filter can remove water andair-borne pathogens such as Legionella.

The present compounds can be employed for reducing the population ofmicrobes, fruit flies, or other insect larva on a drain or othersurface.

The compounds of the present invention can also be employed by dippingfood processing equipment into the use solution, soaking the equipmentfor a time sufficient to sanitize the equipment, and wiping or drainingexcess solution off the equipment, The compound may be further employedby spraying or wiping food processing surfaces with the use solution,keeping the surfaces wet for a time sufficient to sanitize the surfaces,and removing excess solution by wiping, draining vertically, vacuuming,etc.

The compounds of the present invention may also be used in a method ofsanitizing hard surfaces such as institutional type equipment, utensils,dishes, health care equipment or tools, and other hard surfaces.

The antimicrobial compounds can be applied to microbes or to soiled orcleaned surfaces using a variety of methods. These methods can operateon an object, surface, in a body or stream of water or a gas, or thelike, by contacting the object, surface, body, or stream with a compoundof the invention. Contacting can include any of numerous methods forapplying a compound, such as spraying the compound, immersing the objectin the compound, foam or gel treating the object with the compound, or acombination thereof.

A concentrate or use concentration of a compound of the presentinvention can be applied to or brought into contact with an object byany conventional method or apparatus for applying an antimicrobial orcleaning compound to an object. For example, the object can be wipedwith, sprayed with, foamed on, and/or immersed in the compound, or a usesolution made from the compound. The compound can be sprayed, foamed, orwiped onto a surface; the compound can be caused to flow over thesurface, or the surface can be dipped into the compound. Contacting canbe manual or by machine. Food processing surfaces, food products, foodprocessing or transport waters, and the like can be treated with liquid,foam, gel, aerosol, gas, wax, solid, or powdered stabilized compoundsaccording to the invention, or solutions containing these compounds.

Laundry Applications

In some aspects, the compounds and compositions can also be employed inwashing and bleaching and sanitizing or disinfecting or sterilizingarticles, e.g., woven and non-woven textile articles, garments, fabrics,and the like, which have become contaminated. The articles are contactedwith the compositions of the invention at use temperatures in the rangeof about 4° C. to 80° C., for a period of time effective to reducemicrobial populations to the level of sanitizing, disinfecting, orsterilizing the articles. Additionally, in some aspects the compoundsand compositions can be employed as a sporicidal agent.

In other aspects, the compositions can be used to treat articles thatare soiled, stained, in need of refreshing to remove odors, and/or thatare in need of brightening. In yet other aspects, the compositions maybe used to treat articles by introducing a surface enhancing additive tothe article. For example, the compositions may be used to treat anarticle with optical brighteners, water absorption or de-absorptionaides, soil repellents, insecticides, fungicides, anti-wrinkle agents,softeners, odor removal/odor capturing agents, soil shielding/soilreleasing agents, anti-pilling agents, mildew control agents, andcombinations thereof.

In some embodiments, the compositions can be used to wash, bleach and/orantimicrobially treat articles at a temperature of about 30° C. to about50° C. or about 40° C. For example, in some embodiments, the compoundsof the present invention can be injected into a launderingcycle—including but not limited to the pre-wash, wash, souring,extraction, softening, or rinse, or combinations thereof, —waters of alaundry machine and contacted with contaminated fabric for a timesufficient to effect microbial reductions on the fabric; includinginhibition, sanitization, disinfection, sterilization, or as asporicidal agent. Likewise, the compounds and compositions can also beemployed in post washing cycles such as steam tunnels, ironers, ordryers to impart the same antimicrobial and bleaching efficacies. Insome embodiments, the contaminated fabric is contacted with thecompounds and compositions of the present invention for about 5 to about30 minutes. Excess solution can then be removed by rinsing and/orcentrifuging and/or pressing and/or drying the fabric.

In some aspects, the compounds and compositions of the present inventioncan be used as a combination detergent to remove soils from a textilesubstrate, and/or as an antimicrobial agent (including as a sanitizer,disinfectant, sporicidal reduction, or sterilant) and/or as a bleachingagent to whiten or lighten or remove stains from a substrate, e.g., hardsurface, or fabric. Any combination of the aforementioned washingprocesses can be employed in aspects of the present invention. Thecompounds of the present invention can be used to bleach or removestains from any conventional woven or non-woven textile, including butnot limited to, cotton, poly-cotton blends, wool, aramids,polyurethanes, olefins, polyactids, nylons, silk, rayon, flax, jute,acrylics, and polyesters. The compounds of the present invention arealso textile tolerant, i.e., they will not substantially degrade thetextile to which they are applied. The compounds of the presentinvention can be used to remove a variety of stains from a variety ofsources including, but not limited to, cosmetics, lipstick,pigment/sebum, pigment/lanolin, soot, olive oil, mineral oil, motor oil,blood, make-up, red wine, tea, ketchup, mustards, curries, body soils(sebum, urine, fecal matter, etc.), and combinations thereof. It isnoted than when preparing compositions of the invention useful as acombination detergent, bleach, and effective microbial reducer for useon textiles that the composition may be substantially nitrogen-basedchelant free, phosphorous and/or phosphate and/or phosphonate free, andheavy metals—specifically transition metals, post-transition metals, andmetalloids—with an atomic number above 38.

In some aspects, the compounds and compositions of the present inventioncan be used as a bleaching agent to whiten or lighten or remove stainsfrom a substrate, e.g., hard surface, or fabric. The compounds of thepresent invention can be used to bleach or remove stains from anyconventional textile, including but not limited to, cotton, poly-cottonblends, wool, aramids, polyurethanes, olefins, polyactids, nylons, silk,rayon, flax, jute, acrylics, and polyesters. The compounds of thepresent invention are also textile tolerant, i.e., they will notsubstantially degrade the textile to which they are applied. Thecompounds of the present invention can be used to remove a variety ofstains from a variety of sources including, but not limited to,cosmetics, lipstick, pigment/sebum, pigment/lanolin, soot, olive oil,mineral oil, motor oil, blood, make-up, red wine, tea, ketchup,mustards, curries, body soils (sebum, urine, fecal matter, etc.), andcombinations thereof.

In some embodiments, the compounds of the present invention can be usedas a low odor, acidic bleaching and/or detersive agent at an acidic pH,e.g., about 1, 2, 3, and up to about 7. In some embodiments, thecompounds of the present invention can be used as a low odor bleachingagent at a neutral pH, i.e., about 7. In some embodiments, the compoundsof the present invention can be used at an alkaline pH, e.g., about 8,9, or 10. In still yet other embodiments, the compounds of the presentinvention can be used as an acidic bleaching agent that can act as anall in one sour, bleaching and antimicrobial product.

The compounds and compositions of the present invention can be usedalone to treat the articles, e.g., woven or non-woven textiles, or canbe used in conjunction with conventional detergents suitable for thearticles to be treated. The compounds and compositions of the inventioncan be used with conventional detergents in a variety of ways, forexample, the compounds and compositions of the invention can beformulated with a conventional detergent. In other embodiments, thecompounds and compositions of the invention can be used to treat thearticle as a separate additive from a conventional detergent. When usedas a separate additive, the compounds and compositions of the presentinvention can contact the article to be treated at any time. Forexample, the compounds and compositions of the invention can contact thearticle before, after, or substantially simultaneously as the articlesare contacted with the selected detergent.

In some embodiments, when used as a bleaching and/orsanitizing/disinfecting/sporicidal/sterilant agent for a laundryapplication, a compound or mixture of compounds of the present inventionwill be present in a composition at about 5 ppm to about 10,000 ppm. Inother embodiments, when used as a bleaching and/orsanitizing/disinfecting agent for a laundry application, a compound ormixture of compounds of the present invention will be present in acomposition at about 25 ppm to about 5000 ppm. In other embodiments,when used as a bleaching and/or sanitizing/disinfecting agent for alaundry application, a compound or mixture of compounds of the presentinvention will be present in a composition at about 100 ppm up to about1000 ppm. In other embodiments, when used as a bleaching and/orsanitizing/disinfecting agent in a laundry application, a compound ormixture thereof of the present invention will be present at about 20,about 40, about 60, or about 80 ppm. In still yet other embodiments, acompound or mixture of compounds of the present invention itself will beused as a bleaching agent, i.e., the compound or mixture of compoundswill be present in a composition at about 100 wt %.

Clean in Place

Other hard surface cleaning applications for the compounds of thepresent invention include clean-in-place systems (CIP),clean-out-of-place systems (COP), washer-decontaminators, sterilizers,textile laundry machines, ultra and nano-filtration systems and indoorair filters. COP systems can include readily accessible systemsincluding wash tanks, soaking vessels, mop buckets, holding tanks, scrubsinks, vehicle parts washers, non-continuous batch washers and systems,and the like. CIP systems include the internal components of tanks,lines, pumps and other process equipment used for processing typicallyliquid product streams such as beverages, milk, and juices.

Generally, the actual cleaning of the in-place system or other surface(i.e., removal of unwanted offal therein) is accomplished with adifferent material such as a formulated detergent which is introducedwith heated water. After this cleaning step, the instant compositionwould be applied or introduced into the system at a use solutionconcentration in unheated, ambient temperature water. CIP typicallyemploy flow rates on the order of about 40 to about 600 liters perminute, temperatures from ambient up to about 70° C., and contact timesof at least about 10 seconds, for example, about 30 to about 120seconds. The present composition can remain in solution in cold (e.g.,40° F./4° C.) water and heated (e.g., 140° F./60° C.) water. Although itis not normally necessary to heat the aqueous use solution of thepresent composition, under some circumstances heating may be desirableto further enhance its activity. These materials are useful at anyconceivable temperatures.

A method of sanitizing substantially fixed in-place process facilitiesincludes the following steps. The use solution of the invention isintroduced into the process facilities at a temperature in the range ofabout 4° C. to 60° C. After introduction of the use solution, thesolution is held in a container or circulated throughout the system fora time sufficient to sanitize the process facilities (e.g., to killundesirable microorganisms). After the surfaces have been sanitized bymeans of the present composition, the use solution is drained. Uponcompletion of the sanitizing step, the system optionally may be rinsedwith other materials such as potable water. The composition can becirculated through the process facilities for 10 minutes or less.

The present method can include delivering the present composition viaair delivery to the clean-in-place or other surfaces such as thoseinside pipes and tanks. This method of air delivery can reduce thevolume of solution required.

Methods for Contacting a Food Product

In some aspects, the present invention provides methods for contacting afood product with a sulfoperoxycarboxylic acid compounds or compositionemploying any method or apparatus suitable for applying such a compoundor composition. For example, in some embodiments, the food product iscontacted by a compound of the present invention with a spray of thecompound, by immersion in the compound, by foam or gel treating with thecompound. Contact with a spray, a foam, a gel, or by immersion can beaccomplished by a variety of methods known to those of skill in the artfor applying antimicrobial agents to food. Contacting the food productcan occur in any location in which the food product might be found, suchas field, processing site or plant, vehicle, warehouse, store,restaurant, or home. These same methods can also be adapted to apply thecompounds of the present invention to other objects.

The present methods require a certain minimal contact time of thecompound with food product for occurrence of significant antimicrobialeffect. The contact time can vary with concentration of the usecompound, method of applying the use compound, temperature of the usecompound, amount of soil on the food product, number of microorganismson the food product, type of antimicrobial agent, or the like. Theexposure time can be at least about 5 to about 15 seconds. In someembodiments, the exposure time is about 15 to about 30 seconds. In otherembodiments, the exposure time is at least about 30 seconds.

In some embodiments, the method for washing a food product employs apressure spray including a compound of the present invention. Duringapplication of the spray solution on the food product, the surface ofthe food product can be moved with mechanical action, e.g., agitated,rubbed, brushed, etc. Agitation can be by physical scrubbing of the foodproduct, through the action of the spray solution under pressure,through sonication, or by other methods. Agitation increases theefficacy of the spray solution in killing micro-organisms, perhaps dueto better exposure of the solution into the crevasses or small coloniescontaining the micro-organisms. The spray solution, before application,can also be heated to a temperature of about 15 to 20° C., for example,about 20 to 60° C. to increase efficacy. The spray stabilized compoundcan be left on the food product for a sufficient amount of time tosuitably reduce the population of microorganisms, and then rinsed,drained, or evaporated off the food product.

Application of the material by spray can be accomplished using a manualspray wand application, an automatic spray of food product moving alonga production line using multiple spray heads to ensure complete contact,or other spray apparatus. One automatic spray application involves theuse of a spray booth. The spray booth substantially confines the sprayedcompound to within the booth. The production line moves the food productthrough the entryway into the spray booth in which the food product issprayed on all its exterior surfaces with sprays within the booth. Aftera complete coverage of the material and drainage of the material fromthe food product within the booth, the food product can then exit thebooth. The spray booth can include steam jets that can be used to applythe stabilized compounds of the invention. These steam jets can be usedin combination with cooling water to ensure that the treatment reachingthe food product surface is less than 65° C., e.g., less than 60° C. Thetemperature of the spray on the food product is important to ensure thatthe food product is not substantially altered (cooked) by thetemperature of the spray. The spray pattern can be virtually any usefulspray pattern.

Immersing a food product in a liquid stabilized compound of the presentinvention can be accomplished by any of a variety of methods known tothose of skill in the art. For example, the food product can be placedinto a tank or bath containing the stabilized compound. Alternatively,the food product can be transported or processed in a flume of thestabilized compound. The washing solution can be agitated to increasethe efficacy of the solution and the speed at which the solution reducesmicro-organisms accompanying the food product. Agitation can be obtainedby conventional methods, including ultrasonics, aeration by bubbling airthrough the solution, by mechanical methods, such as strainers, paddles,brushes, pump driven liquid jets, or by combinations of these methods.The washing solution can be heated to increase the efficacy of thesolution in killing micro-organisms. After the food product has beenimmersed for a time sufficient for the desired antimicrobial effect, thefood product can be removed from the bath or flume and the stabilizedcompound can be rinsed, drained, or evaporated off the food product.

In other embodiments, a food product can be treated with a foamingversion a the compound of the present invention. The foam can beprepared by mixing foaming surfactants with the washing solution at timeof use. The foaming surfactants can be nonionic, anionic or cationic innature. Examples of useful surfactant types include, but are not limitedto the following: alcohol ethoxylates, alcohol ethoxylate carboxylate,amine oxides, alkyl sulfates, alkyl ether sulfate, sulfonates,including, for example, alkyl aryl sulfonates, quaternary ammoniumcompounds, alkyl sarcosines, betaines and alkyl amides. The foamingsurfactant is typically mixed at time of use with the washing solution.Use solution levels of the foaming agents are from about 50 ppm to about2.0 wt-%. At time of use, compressed air can be injected into themixture, then applied to the food product surface through a foamapplication device such as a tank foamer or an aspirated wall mountedfoamer.

In some embodiments, a food product can be treated with a thickened orgelled version of a compound of the present invention. In the thickenedor gelled state the washing solution remains in contact with the foodproduct surface for longer periods of time, thus increasing theantimicrobial efficacy. The thickened or gelled solution will alsoadhere to vertical surfaces. The compound or the washing solution can bethickened or gelled using existing technologies such as: xanthan gum,polymeric thickeners, cellulose thickeners, or the like. Rod micelleforming systems such as amine oxides and anionic counter ions could alsobe used. The thickeners or gel forming agents can be used either in theconcentrated product or mixing with the washing solution, at time ofuse. Typical use levels of thickeners or gel agents range from about 100ppm to about 10 wt-%.

Methods for Beverage, Food, and Pharmaceutical Processing

The sulfoperoxycarboxylic acid compounds and compositions of the presentinvention can be used in the manufacture of beverage, food, andpharmaceutical materials including fruit juice, dairy products, maltbeverages, soybean-based products, yogurts, baby foods, bottled waterproducts, teas, cough medicines, drugs, and soft drinks. The compoundsof the present invention can be used to sanitize, disinfect, act as asporicide for, or sterilize bottles, pumps, lines, tanks and mixingequipment used in the manufacture of such beverages. Further, thesulfoperoxycarboxylic acid antimicrobial compounds of the presentinvention can be used in aseptic, cold filling operations in which theinterior of the food, beverage, or pharmaceutical container is sanitizedor sterilized prior to filling. In such operations, a container can becontacted with the sanitizing sulfoperoxycarboxylic acid compound,typically using a spray, dipping, or filling device to intimatelycontact the inside of the container with the sulfoperoxycarboxylic acidcompound, for a sufficient period of time to reduce microorganismpopulations within the container. The container can then be emptied ofthe amount of sanitizer or sterilant used. After emptying, the containercan be rinsed with potable water or sterilized water and again emptied.After rinsing, the container can be filled with the beverage, food, orpharmaceutical. The container can then be sealed, capped or closed andthen packed for shipment for ultimate sale. The sealed container can beautoclaved or retorted for added microorganism kill.

In food, beverage, or pharmaceutical manufacturing, fungalmicroorganisms of the genus Chaetomium or Arthrinium, and spores orbacteria of the genus Bacillus spp. can be a significant problem inbottling processes, particularly in cold aseptic bottling processes. Thesulfoperoxycarboxylic acid compounds of the present invention can beused for the purpose of controlling or substantially reducing (by morethan a 5 log₁₀ reduction) the number of Chaetomium or Arthrinium orBacillus microorganisms in beverage or food or pharmaceutical bottlinglines using cold aseptic bottling techniques.

In such techniques, metallic, aluminum or steel cans can be filled,glass bottles or containers can be filled, or plastic (PET or PBT orPEN) bottles, and the like can be filled using cold aseptic fillingtechniques. In such processes, the sulfoperoxycarboxylic acid materialsof the invention can be used to sanitize the interior of beveragecontainers prior to filling with the carbonated (or noncarbonated)beverage. Typical carbonated beverages in this application include, butare not limited to, cola beverages, fruit beverages, ginger alebeverages, root beer beverages, iced tea beverages which may benon-carbonated, and other common beverages considered soft drinks. Thesulfoperoxycarboxylic acid materials of the invention can be used tosanitize both the tanks, lines, pumps, and other equipment used for themanufacture and storage of the soft drink material and also used in thebottling or containers for the beverages. In an embodiment, thesulfoperoxycarboxylic acid sanitizing materials are useful for killingboth bacterial and fungal microorganisms that can be present on thesurfaces of the production equipment and beverage containers.

The sulfoperoxycarboxylic acid compounds of the present invention caneffectively kill microorganisms (e.g., >1 log₁₀ or up to about 5 log₁₀reduction in 30 seconds) from a concentration level of at least about 50ppm, for example, about 150, about 500 ppm or about 1000 ppm of asulfoperoxycarboxylic acid compound. In an embodiment, thesulfoperoxycarboxylic acid compound, excluding water, would be presentat a concentration of about 0.001 to about 1 wt-%, for example, about0.01 to about 0.15 wt-%, or about 0.05 to about 0.1 wt-%.

All acid, salt, base and other ionic and non-ionic forms of thecompounds described are included as compounds of the invention. Forexample, if a compound is shown as an acid herein, the salt forms of thecompound are also included. Likewise, if a compound is shown as a salt,the acid and/or basic forms are also included.

Those skilled in the art will recognize, or be able to ascertain usingno more than routine experimentation, numerous equivalents to thespecific procedures, embodiments, claims, and examples described herein.Such equivalents are considered to be within the scope of this inventionand covered by the claims appended hereto. The contents of allreferences, patents, and patent applications cited throughout thisapplication are hereby incorporated by reference. The invention isfurther illustrated by the following examples, which should not beconstrued as further limiting.

EXAMPLES

Some of the following Examples were performed using a sulfonatedperoleic acid product. Without wishing to be bound by any particulartheory, it is thought that the peracid formed from a commerciallyavailable sulfonated oleic acid starting material includes a mixture ofthe compounds of the present invention. It is thought that this is due,in part, to the nature of the sulfonated oleic acid starting material.That is, it is thought that because the sulfonated oleic acid startingmaterial is derived from naturally occurring sources, it is notchemically pure, i.e., does not contain only one form of the sulfonatedoleic acid. Thus, without wishing to be bound by any particular theoryit is thought that sulfonated peroleic acid (hereinafter referred to asthe “sulfonated peroleic acid product”) used in these examples includeda mixture of about 20-25 wt % Compound A(10-Hydroxy-9-sulfooctadecaneperoxoic acid) about 20-25 wt % Compound N(10,11-dihydroxy-9-sulfooctadecaneperoxoic acid), about 20-25 wt %Compound I (9-Hydroxy-10-sulfooctadecaneperoxoic acid), and about 20-25wt % Compound O (8,9-dihydroxy-10-sulfooctadecaneperoxoic acid). Theremainder of the peracid composition is thought to include about 5 toabout 10 wt % of a mixture of these compounds.

Example 1 Use of a Sulfoperoxycarboxylic Acid as a Coupler Under HighLevel Disinfection Application Conditions

Peroxyoctanoic acid (POOA) stability experiments were performed underhigh level disinfection (HLD) conditions to evaluate the stability of acomposition of the present invention including a sulfonated peroleicacid product, compared with known commercially available disinfectants.

Octave FS®, a peroxyoctanoic containing product, commercially availablefrom Ecolab Inc. was tested against Formulas A, B, and C, and mixturesthereof. Formula A was a mixture of: 2.5 wt % Dequest 2010 (commerciallyavailable from thermPhos), peracid grade; 61 wt % hydrogen peroxide(35%); 2.50 wt % sulfuric acid (98%); 6.0 wt % octanoic acid, 19 wt %Hostapur SAS (40%) (commercially available from Clariant); and 9.00 wt %SXS-40 (commercially available from Stepan Company). Formula B was amixture of about 20 wt % of the sulfonated peroleic acid product, about10% peroctanoic acid, about 15 wt % octanoic acid, and about 0.5 wt %hydrogen peroxide. Formula C was a mixture of about 25 wt % of thesulfonated peroleic acid product, and about 0.50 wt % hydrogen peroxide.Mixtures of Formulas A, B, and C were also tested. The test solutionswere diluted with DI water to make a solution with about 1000 ppm POOApresent at a pH of about 6.5. The table below shows the five solutionstested, and the amount of sulfonated peroleic acid product, POOA, andhydrogen peroxide available in ppm in each of the solutions as tested.

TABLE 2 Test solution composition #1 #2 #3 #4 #5 Octave FS ® (wt %)10.00 0 0 0 0 Formula A (wt %) 0 4.2 0 0 0 Formula B (wt %) 0 0 0.880.55 0.33 Formula C (wt %) 0 0 0.22 0.55 0.77 Final weight with added100 100 100 100 100 DI water (g) Sulfonated peroleic acid 0 0 2318 24592554 product (ppm) POOA (ppm) 1000 1000 800 500 300 H₂O₂ 8050 8928 55 5555

The samples were stored at 40° C. and the amount of POOA present wasmeasured by high performance liquid chromatography at the selectedtimes. The following table shows the results of the HPLC analysis of thesamples at various times.

TABLE 3 Test solution 1 2 3 4 5 Time POOA POOA POOA POOA POOA (hrs)(ppm) (ppm) (ppm) (ppm) (ppm)  0 490 870 700 470 290  6 310 730 590 400250 24 0 120 350 240 150 48 0 10 240 160 100 72 0 0 180 130 80  9 days 00 20 0 0

These results are also graphically depicted in FIG. 1. As can be seenfrom the table above, and FIG. 1, the test solutions including acompound of the present invention, i.e., test solutions 3, 4, and 5,lost less POOA over the course of the first 24 hours compared to theother two test solutions. Even after 48 hours, a greater amount of POOAremained in the test solutions including a compound of the presentinvention, than in the other solutions tested. For each of the testsolutions including a compound of the present invention, it was shownthat the loss of POOA in the solutions was not linear, and that thedecomposition rate of POOA slowed down dramatically at higher ratios ofthe sulfonated peroleic acid product to POOA.

Another stability study was performed to evaluate the stability of acomposition of the present invention at an elevated temperature, i.e.,100° F. A solution including about 2 wt % of the sulfonated peroleicacid product, and about 55 wt % H₂O₂, among other ingredients, was used.The amount of the sulfonated peroleic acid product and H₂O₂ was measuredover the course of 48 days. The results are shown in FIG. 2. As can beseen in this figure, the peracid compound, the sulfonated peroleic acidproduct maintained its activity over the course of the trial, even atthis accelerated temperature.

Yet another stability study was performed to evaluate the stability ofperoxyoctanoic acid when contacted by a compound of the presentinvention, i.e., the sulfonated peroleic acid product, under ambientconditions. For this study, the pH was constant at about 6 to about 6.5.Three different formulas were tested for this study: Formula D includedabout 5 grams of a mixture of the sulfonated peroleic acid product,peroxyoctanoic acid, hydrogen peroxide and sodium cumene sulfate, amongother ingredients; Formula E included about 0.5 g of a mixture of thesulfonated peroleic acid product, and peroxyoctanoic acid; and Formula Fincluded Octave®, commercially available from Ecolab Inc. The amount ofactive peroxyoctanoic acid available at various times over the course of15 days was measured. The results are shown in the table below.

TABLE 4 Time Formula D Formula E Formula F (days) POOA (ppm) POOA (ppm)POOA (ppm) 0 590 640 570 1 550 590 500 4 470 480 360 6 420 400 240 8 410360 160 11 360 270 70 14 310 230 30

These results are also graphically depicted in FIG. 3. As can be seen inthis table, and figure, the formulas including a compound of the presentinvention, i.e., Formulas D and E, retained a higher level of POOA overthe course of 15 days. Thus, without wishing to be bound by anyparticular theory it is thought that the addition of a compositionincluding compounds of the present invention acts to stabilize otherpercarboxylic acids present in the composition.

Example 2 Use of a Sulfoperoxycarboxylic Acid as a Bleaching Agent

The use of a compound of the present invention as a bleaching agent wasevaluated. The soil removal ability of the cleaning composition wasdetermined by washing with artificially soiled fabric swatches. Thesoiled swatches were purchased from a manufacturer or distributor (e.g.Test Fabrics, Inc., West Pittston, Pa.). Soil types such as olive oil,sebum, makeup, wine are characteristic of natural soils found in laundryapplications.

Soiled swatches were washed with the cleaning composition in a devicesuch as a Terg-o-tometer (United States Testing Co., Hoboken, N.J.). TheTerg-o-tometer is a laboratory washing device that consists of multiplepots that reside in a single temperature-controlled water bath, withoverhead agitators under time and speed control. Wash test parametersinclude: wash temperature, wash duration, pH, mechanical agitation, doseof cleaning composition, water hardness, wash formula, and cloth/liquorratio. After completing the appropriate exposure times the fabricsamples were removed. The test chemistries were immediately flushed, andthe swatches rinsed with cold synthetic 5 grain water until 5 cycles offills and rinses were complete. The swatches were then laid flat anddried overnight on white polyester-cotton towels before reflectancereadings were taken using a spectrophotometer, e.g., Hunter Color QuestXE (reflectance) Spectrophotometer.

To determine the percent (%) soil removal (SR), e.g., bleaching ability,the reflectance of the fabric sample was measured on aspectrophotometer. The “L value” is a direct reading supplied by thespectrophotometer. L generally is indicative of broad visible spectrumreflectance, where a value of 100% would be absolute white. The % soilremoval is calculated from the difference between the initial (beforewashing) lightness (L) value and the final L value (after washing):SR=((L _(final) −L _(initial))/(96−L _(initial)))×100%

A bleach test was run comparing a composition including a sulfonatedperoleic acid product with the following commercially availablebleaching/cleaning compositions: Ozonit®, and Oxysan® both availablefrom Ecolab Inc. Ozonit® represents a 4.5% peroxyacetic acid productwhile Oxysan® represents a 0.6% peroxyoctanoic acid product. Formula Awas a composition including about 2 wt % of sulfonated peroleic acidproduct, about 5 wt % peroxyacetic acid and about 1.5 wt % ofperoxyoctanoic acid. Formula A was used at a concentration of 1200 ppmand further treated in two of the three cases with additional aceticacid to produce lowered pH test solutions. Ozonit® was used at aconcentration of 2000 ppm. Oxysan® was tested at concentrations of 1272and 2545 ppm. All of the wash solutions were further treated withDetergent MP® and TurboCharge II®, both available from Ecolab Inc andused at 500 and 750 ppm respectively. The bath/wash temperature wasmaintained at 100° F. Detergent MP® and TurboCharge II provide a commonalkaline builder detergent base. The results from the bleaching test areshown in the table below.

TABLE 5 Stain Removal (%) from Conc. of Cotton Bleach Bleach Type TeaRed Wine Ketchup (mg/L) pH Ozonit ® 29 59 27 2000 9.50 Oxysan ® 21 66 191272 8.00 2X Oxysan ® 33 69 27 2545 8.00 Formula A, pH 8.0 37 73 38 10008.00 Formula A, pH 8.5 38 72 41 1000 8.50 Formula A, pH 9.0 34 69 361000 9.00

As can be seen from this table, the compositions of Formula A achieved ahigher percent stain removal than the commercially available solutionstested at all pH levels tested, especially in the cases of ketchup whichrepresents a hydrophobic stain.

Formula A was also tested using a full scale Wash Wheel Bleach Test. Thetest was run with a commercial 35 lb side loading washing machine(UniMac UX35PVXR). Multipaneled pre-stained test sheets (Ecomon No. 1 &Ecomon No. 4 included 14 bleachable and 12 pigment/unbleachable stainedpanels) were added to the otherwise empty machine before initiating a 20minute washing program (typically at 40° C.). The chemistries were addedin a 30 second staggered sequence via the overhead dispensing cups oncethe machine was filled with 48 L of 5 grain synthetic soft water. Theinitial chemistry added was the alkaline detergent product (about 84 gof Turboemulsion, commercially available from Ecolab Inc.). Thebleaching chemistry was then added ˜30 seconds after thesurfactant-caustic blend and a 20 minute wash cycle was begun. After thewash cycle the machine was drained and 3 rinse cycles were executed. Thesheets were retrieved and air dried at 70° F., overnight beforemeasuring each swatch panel's reflectance with a Hunter Color Quest XE(reflectance) Spectrophotometer (UV filter “IN”). The results are shownin the table below.

TABLE 6 L Reflectance Values Initial ⁵Stain Removal, % stained³Turboemulsion TE + TE + TE + TE + swatch only ⁶Formula A ⁴OzonitFormula A Ozonit Bleachable Stains Tea on CO 80.64 80.67 91.62 88.9471.48 54.01 Tea on PES/CO 80.43 79.24 91.17 88.28 68.96 50.40 Red Wineon CO 73.66 85.94 93.03 92.06 86.72 82.36 Red Wine on PES/CO, aged 73.8282.98 91.71 90.67 80.67 75.97 Coffee on CO 78.92 90.72 93.10 92.70 83.0480.70 Coffee on PES/CO 79.77 92.27 93.62 93.28 85.34 83.26 Black currantjuice on CO 64.40 88.37 93.54 92.82 92.22 89.94 Black currant juice on63.57 85.02 93.30 92.07 91.68 87.89 PES/CO Blood on CO IEC 456, aged46.25 89.51 90.60 91.48 89.14 90.91 Blood on CO IEC 456, not 49.36 93.0693.81 93.88 95.30 95.45 aged Blood/Milk/Ink on CO 45.26 61.00 51.1051.89 11.51 13.06 Cocoa on CO IEC 456, not 75.22 83.76 83.47 83.27 39.7238.74 aged Blood/Milk/Soot on CO 58.87 86.37 69.87 70.54 29.62 31.44Egg/Soot on CO 62.87 76.36 76.09 75.81 39.89 39.05 average/14 66.6583.95 86.15 85.55 68.95 65.23 Unbleachable Stains Pigment/Lanolin on CO71.98 80.90 78.63 80.55 27.70 35.68 Pigment/Lanolin on PES/ 66.65 82.3873.28 81.72 22.60 51.35 CO Pigment/Sebum on CO 73.19 87.70 84.02 86.7647.49 59.48 Pigment/Sebum on PES/ 70.64 87.97 77.82 86.74 28.33 63.49 COSoot/Olive Oil on CO 47.93 69.90 62.45 64.87 30.21 35.23 Soot/Olive Oilon PES/CO 40.77 62.89 56.23 58.57 27.99 32.23 Soot/Mineral Oil on CO59.76 72.35 68.93 71.80 25.30 33.21 Soot/Mineral Oil on PES/ 55.62 80.1573.89 78.78 45.25 57.36 CO Used Motor Oil on CO 65.91 73.06 70.99 71.7716.89 19.47 Used Motor Oil on PES/CO 61.10 68.27 64.08 66.01 8.53 14.08Makeup on CO 84.81 90.06 89.50 90.14 41.94 47.63 Makeup on PES/CO 85.1692.57 91.91 92.14 62.24 64.42 average/12 70.85 86.01 81.49 84.62 32.0442.80 Notes: ³Turboemulsion (TE) is a commercially available all-in-oneemulsion of alkaline metal chelators emulsified with a surfactant blendmade by Ecolab, Inc. and was used in this test at 1750 ppm. ⁴Ozonit is aPeracetic acid-Hydrogen peroxide bleach disinfectant used at aconcentration of 2000 ppm. Ozonit is a blend of Peracetic acid andHydrogen peroxide made by Ecolab, Inc.. ⁵The “Stain Removal, %” wascalculated using the following formula: SR = ((Lfinal − Lintial)/(96 −Lintial)) × 100% CO: Cotton; PES/CO: Polyester-Cotton blend

As can be seen from this table, Formula A averages superior bleaching toOzonit®. Although the superiority on these “bleachable” stains is only3.7 points (5.4%), on those stains which better resist wash removal e.g.tea, the difference was as many as 17 points (24%) higher.

Another full scale wash testing was conducted using a wash wheel (fullsize side loading washing machine), but rather than individual soiledswatches this test utilized multipaneled sheets combining 14“bleachable” stained swatches (Ecomon 4) and a second sheet whichcombined 12 “unbleachable” pigment/hydrocarbon stained swatches (Ecomon1). These panels are custom made for Ecolab by wfk Testgewebe Gmbh ofBruggen, Germany. This extensive bleach test utilized a designexperiment which varied concentrations sometimes simultaneously withtemperatures etc. Following completion of the specified wash time, allEcomon sheets were rinsed thoroughly, dried and their broad spectrumlight reflectivities were measured, again with UV filtering to removalpossible interference from optical brightener effects. Unlike thetergotometer data, the % stain removal wasn't calculated but was ratherdirectly measured from the reflectance instrument (Minolta CM-2610dSpektrophotometer). A “Y” value representing broad spectrum reflectivitywas reported. The higher the “Y” value, the whiter the material, andtherefore, the greater the bleaching or stain removal.

In this test, Formula A was compared to Ozonit®, Ozonit Super® (a 15%peroxyacetic acid product available from Ecolab) and Oxysan® these werevariously combined with the following commercially availablealkaline-builder cleaning agents: Triplex Emulsion®, available fromEcolab Inc.; Turbo Usona®, available from Ecolab Inc.; Ozonit Super®,available from Ecolab Inc.; and Oxysan®, available from Ecolab Inc. Theresults are shown in the tables below.

TABLE 7 Bleaching Results Black Black Currant Tea Tea Red Wine Red WineCoffee Coffee Currant Juice on on on CO on PES/CO on on Juice onProcedure CO PES/CO aged aged CO PES/CO on CO PES/CO Ave. 1.5 ml/l 72.770.0 75.4 74.6 80.2 84.6 82.5 84.1 78.0 ²Triplex Emulsion + 1 ml/lFormula A Conditions: 15′ 40° C. 1.5 ml/l 80.6 79.6 82.5 80.5 83.5 86.085.5 86.1 83.0 Triplex Emulsion + 2 ml/l Formula A Conditions: 15′ 40°C. 1.5 ml/l 82.6 83.1 84.3 80.9 84.3 86.0 86.2 86.3 84.2 TriplexEmulsion + 2.5 ml/l Formula A Conditions: 20′ 40° C. 1.5 ml/l 78.5 79.082.2 82.1 84.8 86.2 86.7 86.5 83.3 Triplex Emulsion + 1 ml/l OzonitSuper Conditions: 10′70° C. 4 ml/l ³Turbo 80.8 80.5 81.5 79.0 81.1 84.282.0 80.8 81.2 Usona + 2 ml/l ⁴Ozonit Performance Conditions: 20′ 40° C.4 ml/l Turbo 79.2 77.9 78.9 76.3 79.9 83.3 77.6 75.9 78.6 Usona + 4 ml/l⁵Oxysan Conditions: 20′ 40° C. 4 ml/l Turbo 82.2 81.7 82.1 80.5 82.685.2 82.6 82.6 82.4 Usona + 2 ml/l Formula A Conditions: 15′ 40° C. LSD1.8 3 1.9 2.4 1.1 0.8 1.7 1.8 1.9

TABLE 8 Bleaching results 4 ml/l 1.5 ml/l 1.5 ml/l 1.5 ml/l 1.5 ml/l³Turbo 4 ml/l 4 ml/l ²Triplex Triplex Triplex Triplex Usona + TurboTurbo Emulsion + Emulsion + Emulsion + Emulsion + 2 ml/l Usona + Usona +1 ml/l 2 ml/l 2.5 ml/l 1 ml/l ⁴Ozonit 4 ml/l 2 ml/l Formula A Formula AFormula A Ozonit Performance ⁵Oxysan Formula A Conditions: Conditions:Conditions: Super Conditions: Conditions: Conditions: 15′ 15′ 20′Conditions: 20′ 20′ 15′ 40° C. 40° C. 40° C. 10′70° C. 40° C. 40° C. 40°C. LSD Pigment/ 54.3 55.6 56.8 67.3 57.5 56.6 54.8 6.1 Lanolin on COPigment/ 53.4 51.4 48.8 60.6 46.1 44.9 46.2 5.8 Lanolin on PES/ COPigment/ 68.3 59.7 59.6 67.5 60.1 58.0 60.9 6.7 Sebum on CO Pigment/66.0 54.2 54.7 73.4 53.2 50.5 54.3 6.3 Sebum on PES/ CO Soot/ 47.7 42.532.2 46.9 24.7 25.1 24.3 7.8 Olive Oil on CO Soot/ 33.8 28.5 24.2 38.415.7 14.4 13.0 9.6 Olive Oil on PES/ CO Soot/ 36.9 34.3 36.0 34.0 33.430.6 30.6 4.5 Min. Oil on CO Soot/ 42.4 43.9 35.8 46.6 31.0 32.7 37.78.2 Min. Oil on PES/ CO Used 42.7 43.9 42.6 46.0 44.0 44.9 46.3 2.6Motor Oil on CO Used 37.7 34.7 33.7 36.4 32.2 33.5 33.8 1.6 Motor Oil onPES/ CO Make 75.3 74.1 75.7 84.1 73.3 72.4 73.5 4 up on CO Make 79.877.9 76.8 86.6 75.7 74.0 76.9 3.8 up on PES/ CO Lipstick 87.6 87.4 87.387.7 85.9 86.9 87.3 1.4 on CO Lipstick 3.0470618 on PES/ CO Average 53.250.1 48.1 57.3 45.6 44.8 46.0 5.6 Notes: ¹Y-value refers to areflectance value calculated by the Minolta CM-2610d Spektrophotometer.It is very similar to the L-value calculated by the Hunter Lab'sSpectrophotometers. ²Triplex Emulsion is a commercially availableall-in-one emulsion of alkaline metal chelators emulsified with asurfactant blend made by Ecolab, Inc. (Europe). ³Turbo Usona is acommercially available all-in-one emulsion of alkaline metal chelatorsemulsified with a surfactant blend made by Ecolab, Inc. (Europe).⁴Ozonit Super is a Peracetic acid-Hydrogen peroxide bleach disinfectant,made by Ecolab, Inc. (Europe). ⁵Oxysan is a Peracetic acid-Hydrogenperoxide bleach disinfectant which also contains Peroxyoctanoic acid,and is made by Ecolab, Inc. (Europe). CO: Cotton PES/CO:Polyester-Cotton blend

As can be seen from these results, overall the samples washed withcompositions of the present invention, i.e., Formula A, achieved similarbleaching compared with commercially available bleaching agents.

Example 3 Use of a Sulfoperoxycarboxylic Acid as a Bleaching Agent

A bleach test was run comparing a composition including asulfoperoxycarboxylic acid of the present invention, i.e.,11-sulfoundecaneperoxoic acid (Compound D) with the followingcommercially available bleaching/cleaning compositions: Tsunami 100®,available from Ecolab Inc.; Oxonia Active®, available from Ecolab Inc.;hydrogen peroxide (35%); and PAP-70®, available from Solvay. Thesechemistries were used as is except for pH adjustments to pH 8 usingsodium bicarbonate, and pH 12 by the addition of sodium hydroxide, in 5grain hard water.

Fabric swatches soiled with tea, blood, or wine were used for thisexample. The soil swatches were washed using the same experimentalprocedure described above in Example 2. However, for this example, thesoil swatches were washed for 10 minutes at 120° F. The pH of the washsolution for all samples was about 9. The percent soil removal (SR) wasdetermined according to the method described above in Example 2. Thefollowing table shows the results of this study.

TABLE 9 Use Solution Wash Bleach Available Time mg/L use Oxygen BleachType pH Temp (F.) (min) % SR solution (ppm) Removal of Tea StainsComposition 9 120 10 37 1350 56 Including Compound D Tsunami 9 120 10 34770 56 100 ® Oxonia 9 120 10 27 410 56 Active ® H₂O₂ (35%) 9 120 10 24340 56 PAP-70 9 120 10 63 1386 56 Water 9 120 10 11 0 56 (control)Removal of Blood Stains Composition 9 120 10 90 1350 56 IncludingCompound D Tsunami 9 120 10 81 770 56 100 ® Oxonia 9 120 10 80 410 56Active ® H₂O₂ (35%) 9 120 10 82 340 56 PAP-70 9 120 10 88 1386 56 Water9 120 10 36 0 0 (control) Removal of Red Wine Stains Composition 9 12010 62 1350 56 including Compound D Tsunami 9 120 10 57 770 56 100 ®Oxonia 9 120 10 41 410 56 Active ® H₂O₂ (35%) 9 120 10 45 340 56 PAP-709 120 10 74 1386 56 Water 9 120 10 36 0 56 (control)

As can be seen from this table, with respect to tea stains, the PAP-70®composition achieved the greatest soil removal. The compositioncontaining a compound of the present invention achieved the next highestpercent soil removal. With respect to blood stains, the compositioncontaining the sulfoperoxycarboxylic acid of the present inventionachieved the greatest soil removal. However, all concentrated oxidizersperformed well in removing the blood stains. With respect to the redwine stains, the sulfoperoxycarboxylic acid of the present inventionperformed well compared to the PAP-70®.

Example 4 Stability Studies

The stability of a sulfoperoxycarboxylic acid of the present invention,i.e., 11-sulfoundecaneperoxoic acid (Compound D), was compared to thatof phthalimidoperoxyhexanoic acid (PAP). The stability data for the PAPsample were taken from U.S. Pat. No. 5,994,284, assigned to ClariantGmbH. Samples of the compound of the present invention were stored forfour (4) weeks at various temperatures. The loss of active oxygen wasmeasured by titrimetry. The results are shown in the table below.

TABLE 10 Temperature Loss of Active Compound Storage Time (weeks) (° C.)Oxygen (%) Compound D 4 Room Temp. 0.78 Compound D 4 38 7.9 Compound D 450 15.7 PAP 4 25 1.4 PAP 4 40 2.0 PAP 4 50 12.0

As can be seen from this table, the compound of the present inventionwas more stable, i.e., lost less active oxygen, at room temperature,i.e., about 23° C., than the PAP at 25° C.

Example 5 Bleaching Performance of Various Formulas of the PresentInvention

A test was run to compare the bleaching properties of compositions ofthe present invention with the following commercially availablebleaching agents: Ozonit®, available from Ecolab Inc.; and PAP®,available from Clariant. The following compositions of the presentinvention were used: Formula A, which included about 25 wt % of thesulfonated peroleic acid product, about 70 wt % H₂O₂ (35%), and about 5wt % HEDP 60; Formula B which included about 24 wt % of a mixture of thesulfonated peroleic acid product and peroxyoctanoic acid, about 72 wt %H₂O₂ (35%), and about 4 wt % HEDP 60; and Formula C which included about20 wt % of a mixture of the sulfonated peroleic acid product andperoxyoctanoic acid, about 62 wt % H₂O₂ (35%), about 4 wt % HEDP 60, andabout 13 wt % acetic acid. These formulas were compared with thecommercially available bleaching agents at 40° C. at a pH of between 7to 8. The Ozonit® was also tested at 60° C.

To measure the bleaching ability of the formulations, a bleaching testas described in Example 2 was performed. The results are shown in FIG.4. As can be seen in this figure, Formulas A, B and C had far superiorbleaching ability compared to Ozonit® at 40° C. When the Ozonit® wasused at 60° C., Formulas A, B, and C had very similar bleaching ability.Formula C also had similar bleaching performance compared to the PAP.Thus, Formulas A, B, and C showed equal, if not better, bleachingproperties compared to known commercially available bleaching agents at40° C.

Example 6 Antimicrobial Studies

(a) Bactericidal Efficacy

An experiment was performed to determine the bactericidal efficacy of acomposition according to the present invention, with and without asurfactant, as compared to other commercially available products.Formula A included about 1190 ppm of a sulfonated peroleic acid product,as well as peroxyoctanoic acid, and peracetic acid. The surfactant usedfor this example was Turboemulsion® (TE), commercially available fromEcolab Inc. The compositions were tested against Clostridium difficileATCC 9689, MRSA ATCC 33592, Enterococcus hirae ATCC 10541, Escheria coliATCC 11229, and Pseudomonas aeruginosa ATCC 15442, at 5 and 60 minuteexposure times. The commercially available compositions, Ozonit®, andPAP were also tested. The following formulations were tested:

TABLE 11 Test Use Solution Desired (Volume of Test Test Concentration ofSubstance/Total Formulation Active Agent Diluent Volume) pH Formula A1190 ppm Sterile 0.194 g Formula A + 7.59 with MilliQ 170 μL TE/100 gsurfactant Water Formula A 1190 ppm 0.194 g Formula A/ 8.53 without 100g Surfactant PAP ® 1820 ppm 0.182 g PAP + 1.5 g 8.50 TE/100 g Ozonit ®2000 0.200 g Ozonit + 1.5 g 7.21 TE/100 g

The test method followed was according to European Standard EN 13704:Quantitative Suspension Test for the Evaluation of Sporicidal Activityof Chemical Disinfectants and Antiseptics Used in Food, Industrial,Domestic and Institutional Areas. Generally, a test suspension ofbacterial spores in a solution of interfering substance, simulatingclean conditions, was added to a prepared sample of the test formulationdiluted in hard water. The mixture was maintained at the specifictemperature and time desired. At this contact time, an aliquot is taken;the sporicidal action in this portion was immediately neutralized orsuppressed by a validated method. The number of surviving bacterialspores in each sample was determined and the reduction in viable countswas calculated.

The disinfectant properties of each of the formulations at 5 minutes at40° C. are shown below in Table 12.

TABLE 12 Formula A Formula A with without Test/System Surfactant PAPOzonit Surfactant MRSA >6.66 >6.66 >6.66 >6.66Enterococcus >6.26 >6.26 >6.26 >6.26 hirae ATCC 10541Escherichia >6.74 >6.74 >6.74 >6.74 coli ATCC 11229Pseudomonas >6.32 >6.32 >6.32 >6.32 aeruginosa ATCC 15442Clostridium >3.87 1.17 2.57 3.09 difficile ATCC 9689

As can be seen from this table, the compositions of the presentinvention that were tested were as effective as a disinfectant as thecommercially available formulations tested. Further, with respect toClostridium difficile, the compositions of the present invention weremore effective than the commercially available products tested.

(b) Stability and Sporicidal Efficacy at 14 Days

A test was run to determine the stability and sporicidal efficacy of acomposition of the present invention against spores. The compositiontested included the sulfonated peroleic acid product, and an amount ofperoxyoctanoic acid. The test method used was the European Standard EN13704: Quantitative Suspension Test for the Evaluation of SporicidalActivity of Chemical Disinfectants and Antiseptics Used in Food,Industrial, Domestic and Institutional Areas, described above. The tablebelow shows the results of this study.

TABLE 13 Sulfonated Peroleic Acid Product + POOA (14 Day Retention) DIWater pH 6.5 B. subtilis C. difficile Clean Conditions 20° C. 60 min 60min Log reduction 3.84 Log reduction 2.71

A composition including 30 ppm peroxyoctanoic acid was also tested. Thecomposition of peroxyoctanoic acid alone did not result in a reduction.

FIG. 5 shows the stability impact that the compound of the presentinvention used, i.e., the sulfonated peroleic acid product, had on theamount of POOA over time during this study. As can be seen from thisfigure, the amount of POOA available over time was higher with thesample of POOA that was stabilized using a composition of the presentinvention, compared to a sample of POOA that was not stabilized using acomposition of the present invention.

(c) Synergistic Effect of a Composition of the Present Invention with aKnown Sanitizes

For this study, the ASME 1052-96: Standard Test Method for Efficacy ofAntimicrobial Agents against Viruses in Suspension was used. Acomposition including 1000 ppm peroxyacetic acid (POAA) was testedalone, and in combination with sulfonated peroleic acid product.

The POAA solution alone did not display complete inactivation ofPoliovirus Type 1 after an exposure time of four minutes. The reductionsin viral titer were ≦0.75 and ≦0.50 log 10. When the POAA solution wastested with 1000 ppm of the sulfonated peroleic acid product, thesolution displayed complete inactivation of Poliovirus Type 1 after anexposure time of a few minutes, and was therefore efficacious againstthe virus. The reduction in viral titer was ≧5.75 log 10.

(d) Synergistic Effect of a Compound of the Present Invention withPeroxyoctanoic Acid

For this study, the MS103: Quantitative Tuberculocidal Test was used.The sulfonated peroleic acid product was tested alone, and incombination with peroxyoctanoic acid at various concentrations againstMycobacterium bovis BCG. The compositions were tested at a pH of 6.5 atroom temperature. The results are shown in the table below.

TABLE 14 Log Test Substance Exposure Time Reduction 1000 ppm SulfonatedPeroleic 2.5 min 4.46 Acid Product   5 min 5.11 300 ppm POOA 2.5 min3.48   5 min <4.31 1000 ppm Sulfonated Peroleic 2.5 min >7.31 AcidProduct and   5 min >7.31 300 ppm POOA 1000 ppm Sulfonated Peroleic 2.5min ≧7.31 Acid Product and   5 min >7.31 150 ppm POOA

As can be seen from this table, the samples treated with both acomposition of the present invention including the sulfonated peroleicacid product, and POOA had a higher log reduction of Mycobacterium bovisBCG than those samples treated with either the sulfonated peroleic acidproduct or POOA alone. Although it was found that the samples treatedwith just the sulfonated peroleic acid product did have a higher logreduction of bacteria than the samples treated with just POOA.

(e) Use of a Compound of the Invention as a Hospital Disinfectant

For this test, the AOAC Official Method 955.15—Testing DisinfectantAgainst Staphylococcus aureus and the AOAC Official Method964.02—Testing Disinfectants Against Pseudomonas aeruginosa were used.The composition used included the sulfonated peroleic acid product, andperoxyoctanoic acid (POOA), at various concentrations. The followingchart summarizes the test procedure used, and the results.

TABLE 15 Dilution (Volume of Test Desired Test System/ SubstanceConcentration Diluent Total Volume) Test pH Sulfonated 1000 ppm 400 ppm2.910 g Sulfonated 6.5 Peroleic Sulfonated Synthetic Peroleic Acid AcidPeroleic Acid Hard Product + 0.2345 g Product + Product Water POOA/1500g POOA 300 ppm POOA 1000 ppm 0.1852 g Sulfonated 6.5 Sulfonated PeroleicAcid Peroleic Acid Product +0.4690 g Product POOA/1500 g 150 ppm POOA #Negative Tubes/ Test system Test Substance # Carriers TestedStaphylococcus aureus 1000 ppm Sulfonated 60/60 ATCC 6538 Peroleic AcidProduct + 300 ppm POOA Staphylococcus aureus 1000 ppm Sulfonated 60/60ATCC 6538 Peroleic Acid Product + 150 ppm POOA Pseudomonas aeruginosa1000 ppm Sulfonated 60/60 ATCC 15442 Peroleic Acid Product + 300 ppmPOOA Pseudomonas aeruginosa 1000 ppm Sulfonated 60/60 ATCC 15442Peroleic Acid Product + 150 ppm POOA

As can be seen from this table, the compositions tested were effectiveagainst each of the test systems.

Example 7 Coupling Abilities of Compounds of the Present Invention

The ability of a composition of the present invention including thesulfonated peroleic acid product to couple octanoic acid was compared tothe coupling abilities of two known commercially available couplingagents, NAS and linear alkylbenzene sulphonate (LAS).

The results can be seen in FIG. 6. As can be seen from this figure, onegram of the sulfonated peroleic acid product was able to couple twice asmuch octanoic acid compared to the other coupling agents tested.

Example 8 Formation of Sulfonated Carboxylic Acids and theirPercarboxylic Salts

A study was run to determine the effect of the position of the sulfonategroup on the carboxylic acid in forming a peracid. Specifically, a studywas run to determine whether having the sulfonate group at the αposition prohibits the oxidation and/or perhydrolysis of the carboxylicacid group to form the corresponding peroxycarboxylic acid.

Commercially available sulfonated fatty acid salts (methyl esters) arepredominantly α sulfonated, including, for example, Alpha-Step PC-48(commercially available from the Stepan Comp.), Alpha-Step MC-48(MC-48)(commercially available from the Stepan Comp.), Alpha-Step BSS-45(commercially available from the Stepan Comp.), and MES (commerciallyavailable from the Lion Corporation). Structurally, these compounds aresodium alphasulfo methyl C₁₂-C₁₈ esters and disodium alphasulfo C₁₂-C₁₈fatty acid salts. Their structures are shown below:

Sulfonated oleic acid is another commercially available sulfonated fattyacid. These compounds are mainly 8-sulfo-octadecenoic acid salts, with aminority of 9-sulfo-10-hydroxy-octadecanoic acid salts. They are notsulfonated at the α position. The structures of these types of compoundsare shown below:

α-sulfonated fatty acids were prepared by the hydrolysis of the mixtureof α-sulfonated fatty acid methyl ester and the acid (MC-48). To abeaker containing 25 g of MC-48, 12 g of 50% NaOH solution was added.The mixture was stirred at ambient temperatures for 3 hours. The mixturewas then acidified by adding H₂SO₄ (50%) until the pH of the mixturereached about 0-1. The white solid precipitate was filtered, washed withcold water, and dried. The white solid powder yield was evaluated using¹³C NMR (DMSO-d₆). The methyl group of the methyl ester in the rawmaterial was not observed, indicating complete hydrolysis.

In order to try and form the peracid using an acid catalyzed hydroxidereaction the following reaction was performed. 0.5 g of the MC-48derived fatty acid sulfonate, as prepared above, was weighed into a 50ml beaker. To this beaker, 30 g of H₂O₂ (35%) was added. then, 5 g ofH₂SO₄ (985) was slowly added, producing a clear solution. After sittingat 50° C. for 24 hours, the solution was analyzed to determine thepresence of a peracid.

To determine the presence of a peracid, a kinetic iodometric titrationsimilar to the method disclosed in Sully and Williams (“The Analysis ofPer-Acids and Hydrogen Peroxide,” The Analyst, 87:1037, p. 653 (August1962)) was used. This method has demonstrated a lower detection limit ofabout 0.3 ppm for POAA. Given the molecular weight ratio of POAA to theperspective percarboxylic acid of PC-48, the detection limit wasestimated to be about 1.4 ppm (3.93×10⁻⁶ M). No peracid formation wasobserved. This is equivalent to a percarboxylic acid formation constant(Keq) less than 0.002, suggesting substantially no peracid was formed.

Alternatively, formation of the peracid was determined using ¹³C NMR(D₂O). Using this technique, no carbonyl resonance signal from theperacid was observed.

Other α-sulfonated fatty acid sources such as Alpha-Step PC-48 andAlpha-Step BSS-45 were also reacted with H₂O₂ in a similar manner, andin both cases, no corresponding peracids were detected.

Non-α-sulfonated fatty acids were also tested to determine thelikelihood of peracid formation. For the sulfonated oleic acid discussedabove, the measured formation constant was 1.42. The sulfonatedundecenoic acid was collected as a stable solid powder, so the formationconstant was not measured. Although the formation constant of theperacid of sulfonated oleic acid is significantly lower than that of themost common commercialized peracid, peroxyacetic acid (Keq=2.70), it isstill high enough to make practical yields.

Overall, without wishing to be bound by any particular theory, it isthought that the α-sulfo group prohibits the oxidation and/orperhydrolysis of the carboxylic acid group by H₂O₂ to the correspondingperacid. This may in part be due to its strong electron withdrawingeffects.

Example 9 Clean in Place Sanitizing Compositions

A study was run to determine the efficacy of compositions of the presentinvention as sanitizers used in a clean in place cleaning method. Acomposition including about 5.85 wt % of the sulfonated peroleic acidproduct, and about 11.6% hydrogen peroxide, about 1 wt % of a chelatingagent, about 12.75 wt % of H₂SO₄, about 13.6 wt % NAS-FAL (sodium octanesulfonate), and about 1.5 wt % of SXS (commercially available from theStepan Company) was prepared. Synthetic hard water was used to dilutethe test composition to the desired peracid concentration. The peracidwas tested at concentrations of 1000 ppm, 750 ppm and 500 ppm. The pH ofthe use solutions were as follows:

Concentration of Peracid in Use Solution pH  500 ppm peracid 1.65  750ppm 1.46 1000 ppm 1.38

The use solutions were tested against Staphylococcus aureus ATCC 6538and Pseudomonas aeruginosa ATCC 15442. The organic soil used was 5%Fetal Bovine Serum. The exposure time of the test was 5 minutes at atemperature of 20±1° C. A neutralizer screen was also performed as partof the testing to verify that the neutralizer adequately neutralized theproduct and was not detrimental to the tested organisms. The plates wereincubated at 35° C. for 48 hours with the test systems prior to exposureto the peracids. The results are shown in the table below.

TABLE 16 Test Substance # Negative Tubes/# Carriers TestedStaphylococcus aureus ATCC 6538 1000 ppm Peracid Composition 60/60Pseudomonas aeruginosa ATCC 15442 1000 ppm Peracid Composition 60/60Test Controls Control Test System Results Negative Carrier 1 negative of1 tested Positive Carrier Staphylococcus aureus 1 positive of 1 testedATCC 6538 Positive Carrier Pseudomonas aeruginosa 1 positive of 1 testedOrganic Soil ATCC 15442 1 negative of 1 tested NeutralizationStaphylococcus aureus 6 positive of 6 tested (1000 ppm) ATCC 6538Neutralization Pseudomonas aeruginosa 6 positive of 6 tested (1000 ppm)ATCC 15442 Culture Enumeration Staphylococcus aureus 9.0 × 10⁸ CFU/mLATCC 6538 Culture Enumeration Pseudomonas aeruginosa 1.0 × 10⁹ CFU/mLATCC 15442 Carrier Enumeration Staphylococcus aureus 1.0 × 10⁶ CFU/mLATCC 6538 1.0 × 10⁷ CFU/Carrier Carrier Enumeration Pseudomonasaeruginosa 2.3 × 10⁶ CFU/mL ATCC 15442 2.3 × 10⁷ CFU/Carrier TestSubstance # Negative Tubes/# Carriers Tested Staphylococcus aureus ATCC6538 500 ppm Peracid Composition 59/60 750 ppm Peracid Composition 60/60Pseudomonas aeruginosa ATCC 15442 500 ppm Peracid Composition 58/60 750ppm Peracid Composition 60/60 Test Controls Control Test System ResultsNegative Carrier 1 negative of 1 tested Positive Carrier Staphylococcusaureus 1 positive of 1 tested ATCC 6538 Positive Carrier Pseudomonasaeruginosa 1 positive of 1 tested Organic Soil ATCC 15442 1 negative of1 tested Neutralization Staphylococcus aureus 3 positive of 3 testedATCC 6538 Neutralization Pseudomonas aeruginosa 3 positive of 3 testedATCC 15442 Culture Enumeration Staphylococcus aureus 1.0 × 10⁹ CFU/mLATCC 6538 Culture Enumeration Pseudomonas aeruginosa 1.0 × 10⁹ CFU/mLATCC 15442 Carrier Enumeration Staphylococcus aureus 7.2 × 10⁵ CFU/mLATCC 6538 7.2 × 10⁶ CFU/Carrier Carrier Enumeration Pseudomonasaeruginosa 2.0 × 10⁶ CFU/mL ATCC 15442 2.0 × 10⁷ CFU/Carrier

As can be seen from these results, the use solutions tested wereeffective disinfectants against both Staphylococcus aureus, andPseudomonas aeruginosa at the concentrations tested.

Another study was run to determine the sanitizing efficacy of the testsolution against Staphylococcus aureus ATCC 6538 and Escherichia coliATCC 11229 after a 30 second exposure time. For this experiment thesolutions were diluted to have a concentration of 50 ppm, 75 ppm or 100ppm of the sulfonated peroleic acid product. The pH of the use solutionswere as follows:

Concentration of Peracid in Use Solution pH  50 ppm peracid 2.70  75 ppm2.47 100 ppm 2.30

The use solutions were tested against Staphylococcus aureus ATCC 6538and Escherichia coli ATCC 11229. The exposure time was 30 seconds at atemperature of 25±1° C. A neutralizer screen was also performed as partof the testing to verify that the neutralizer adequately neutralized theproduct and was not detrimental to the tested organisms. The plates wereincubated at 35° C. for 48 hours with the test systems prior to exposureto the peracids. The results are shown in the table below.

TABLE 17 Inoculum Numbers Average Log₁₀ Test System CFU/mL Log₁₀ GrowthGrowth Staphylococcus aureus 107 × 10⁶, 109 × 10⁶ 8.03, 8.04 8.04 ATCC6538 Escherichia coli 138 × 10⁶, 151 × 10⁶ 8.14, 8.18 8.16 ATCC 11229Average Log Survivors Log₁₀ Log₁₀ Re- Test Substance (CFU/mL) GrowthGrowth duction Staphylococcus aureus ATCC 6538  50 ppm Peracid 28 × 10¹,20 × 10¹ 2.45, 2.30 2.38 5.66 Composition  75 ppm Peracid  0 × 10¹, 100× 10¹ <1.00, 3.00   <2.00 >6.04 Composition 100 ppm Peracid  0 × 10¹, 0× 10¹ <1.00, <1.00 <1.00 >7.04 Composition Escherichia coli ATCC 11229 50 ppm Peracid  0 × 10¹, 2 × 10¹ <1.00, 1.30   <1.15 >7.01 Composition 75 ppm Peracid  0 × 10¹, 0 × 10¹ <1.00, <1.00 <1.00 >7.16 Composition100 ppm Peracid  0 × 10¹, 0 × 10¹ <1.00, <1.00 <1.00 >7.16 Composition

As can be seen from these results the use solutions tested wereeffective sanitizers against both Staphylococcus aureus and Escherichiacoli. The test solution containing 100 ppm of the sulfonated peroleicacid product was the most effective sanitizer.

Example 10 Foam Properties of Selected Compositions of the PresentInvention

A study was performed to determine the foam properties of selectedcompositions of the present invention, compared to compositionsincluding commercially available surfactants. The following compositionswere prepared: Formula A included 50 ppm of the sulfonated peroleic acidproduct at a pH of 2.48; Formula B included 50 ppm of the sulfonatedperoleic acid product at a pH6.75; Formula C included 64 ppm of acommercially available sulfonated oleic acid (SOA)(Lankropol OPA (50%)available from Akzo Nobel) at a pH of 2.48; Formula D included 64 ppm ofa commercially available sulfonated oleic acid (Lankropol OPA (50%)available from Akzo Nobel) at a pH of 6.56; Formula E included 128 ppmof a commercially available sulfonated oleic acid (Lankropol OPA (50%)available from Akzo Nobel) at a pH of 2.48; Formula F included 128 ppmof a commercially available sulfonated oleic acid (Lankropol OPA (50%)available from Akzo Nobel) at a pH of 7.20; and Formula G included 93ppm of sodium octane sulfonate (NAS) (commercially available fromEcolab) at a pH of 2.48. The foam heights were determined using thefollowing method. First 3000 ml of each formula was prepared and gentlypoured into Glewwe cylinder. A ruler was attached to the side of thecylinder, and the solution was level with the bottom of the ruler. Thepump was turned on. Foam height was estimated by reading the averagelevel of foaming according to the ruler. Foam height readings were takenversus time with a stopwatch or timer. The pump was turned off andheight of the foam was recorded at various times. The results are shownin the table below.

TABLE 18 Pump On Time (sec) Pump Off Time (sec) 30 60 300 30 60 300 FoamFoam Foam Foam Foam Foam Height Height Height Height Height HeightSample (inches) (inches) (inches) (inches) (inches) (inches) Formula A2.5 3.8 5.5 3.5 2.0 0.5 Formula B 1.5 2.0 2.5 0.2 <0.1 NA Formula C 4.06.2 9.2 8.7 8.5 5.5 Formula D 3.1 4.5 10 9.8 8.5 4.0 Formula E 2.6 4.58.5 8.2 8.0 5.0 Formula F 0.15 0.15 0.2 <0.1 <0.1 <0.1 Formula G 1.0 1.01.2 0.4 0.2 <0.1

As can be seen from these results, the formulas including compositionsof the present invention, i.e., Formulas A and B had much lower foamheights than Formulas C and D which included the non-peracid form of thesulfonated material, i.e., sulfonated oleic acid. The reduced foamheight of the compositions of the present invention is useful when usingthe compositions in applications where the production of foam isdetrimental to the application, for example, in a clean in placecleaning and/or sanitizing application.

Example 11 Laundry Sanitizing Compositions

A study was run to determine the ability of a composition of the presentinvention to sanitize laundry. A composition containing the sulfonatedperoleic acid product was tested against the commercially availablecleaning compositions Ozonit®, commercially available from Ecolab Inc.,and PAP-70®, available from Solvay. The compositions were tested againstStaphylococcus aureus ATCC 6538 and Pseudomonas aeruginosa ATCC 15442 at104° F. for 6 minutes. The test method was as follows. Fabric samplesthat had been rinsed with boiling water containing 300 grams sodiumcarbonate and 1.5 grams of a non-ionic wetting agent (e.g., TritonX-100), followed by a cold water rinse until all visible traces of thewetting agent were removed, were obtained. The fabric samples wereallowed to completely dry. The fabric samples were then autoclaved tosterilize them.

The test substances were then prepared, and the fabric samples wereinoculated with the test substances. The inoculated swatches were thendried. The samples were then secured in a laundrometer and agitated inwash water. The wash water was removed from the chamber of thelaundrometer, and the wash water and fabric samples are evaluated forthe reduction of the tested microorganism population.

The results are shown in the table below.

TABLE 19 Composition including Sulfonated Test/System Peroleic AcidProduct PAP-70 ® Ozonit ® Sanitizer Screen >3.82 >3.82 NA Disinfectant 9negative/9 total 9 negative/ 5 negative/ (Cloth Carrier 9 total 9 totalScreen)

As can be seen from these results, both the composition of the presentinvention tested showed a greater than 3 log reduction in both the washwater and fabric carriers against P. aeruginosa and on the fabriccarriers against S. aureus.

The present invention also relates to novel compounds and the synthesisthereof. Accordingly, the following examples are presented to illustratehow some of those compounds may be prepared.

Example 12 Stability Study

A study was performed to determine the stability of various sulfonatedperacids in aqueous solutions. The sulfonated peracids were comparedunder the same controlled conditions to determine how the structuraldifferences of the selected peracids impacted stability. The sulfonatedperacids studied included both mid-chain sulfonated and terminallysulfonated peracids.

Each peracid was tested at a concentration of 50 ppm under ambientconditions. Each individual solution was prepared from the correspondingperacid concentrate by adding it to a 0.05 M pH 5.0 citrate buffer, andadjusting the final solution pH to 5.0 with the addition of a smallamount of caustic. The terminally sulfonated peracids studied are shownin the table below.

Name Structure 2-Sulfoperoxyacetic acid (2-SPOAA)

5-sulfoperoxyheptanoic acid (5-SPOHA)

6-sulfoperoxyhexanoic acid (6-SPOHXA)

11-sulfoperoxyundecanoic acid (11- SPOUA)

The above terminally sulfonated peracids were compared to the mid-chainsulfonated peracid, persulfonated oleic acid product (PSOA), describedabove.

It should be noted however, that the precursor for the 11-SPOUA, viz.11-sulfoundecanoic acid, has limited solubility so less of the precursorwas used to make the sulfonated peracid studied. The same amount ofprecursor acid was used for making each of the other sulfonated peracidstested.

The peracid concentration over time was measured using a kineticiodometric titration method. The stability of each of the sulfonatedperacids is shown in FIG. 7. For comparison, 50 ppm peroxyacetic acid(POAA), at the same concentration and under the same conditions, wasalso included in the stability study. Based on the results seen in FIG.7, the half time of each individual peracid was estimated and theresults are summarized in the table below.

TABLE 20 Peracid POAA 2-SPOAA 5-SPOHA 6-SPOHXA 11-SPOUA PSOA t_(1/2)(hours) 115 37 110 88 91 155

As can be seen from the table above, 5-SPOHA, 6-SPOHXA, and 11-SPOUAhave similar stability profiles in aqueous solutions compared to that ofPOAA. The 2-SPOAA had a significantly shorter half life time.

Also as can be seen from these results, the stability of the mid-chainsulfonated PSOA was significantly better than that of POAA under thetested conditions. Without wishing to be bound by any particular theory,it is thought that the PSOA is the only peracid tested which hasdetergency, and which will form a micelle in an aqueous solution. Giventhat the sulfo group in the mid-chain sulfonated PSOA, is located nearthe center of the molecule, it is thought that the peroxycarboxylicportion is protected within a generally hydrophobic domain of vesiclesor related microstructures when PSOA is dissolved in water. This resultsin a substantially greater stability and longer half-life than theterminally sulfonated peracids.

Example 13 Bleaching Study

A study was performed to determine the bleaching properties of varioussulfonated percarboxylic acids in aqueous solutions. The sulfonatedperacids were compared to a surfactant/builder only control, as well asto peroxyacetic acid.

The following sulfonated peracids were tested: 2-Sulfoperoxyacetic acid(2-SPOAA); 5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoicacid (6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); andsulfonated peroleic acid product (PSOA). The individual sulfonatedperacids were made, and allowed to incubate/equilibrate at 40° C. for 5to 7 days. After determining the peracid concentrations, the respectiveperacid solutions were normalized for potential available oxygen asdelivered by the peracids only. These solutions were tested for theirbleaching power at 100° F., pH 7 and in 5 grain hard water over a 20minute exposure. The table below shows the initial available oxygen fromeach peracid, as well as the percent of peracid titrated

TABLE 21 2- 5- 6- 11- Buffer Composition POAA* SPOAA SPOHA SPOHXA SPOUAPSOA Control Available Oxygen 32840 620 1300 1100 400 760 0 measured inperoxyacids' bleach concentrates formulae (ppm) Concentrate sample 0.1910.00 4.81 5.70 15.60 8.20 0 bleach solution Wt (g) Volume of buffer5.00** 5.00 5.00 5.00 5.00 5.00 5.00 concentrate used (8.5%/8.5%,NaHCO₃/ Na₂CO₃) (mL) Diluent (DI-H2O) mL 120 120 120 120 120 120 120Available Oxygen from 50 50 50 50 50 50 0 peroxyacids in bleachsolutions Total Bleach Use- 125 125 125 125 125 125 125 Solution Volume(mL) *POAA: Peroxyacetic acid **Required additional Acetic acid to reachpH target~7.0

The sulfonated peracids were evaluated for their bleaching properties(also referred to herein as “soil removal” properties) by exposingsoiled swatches including: tea on 100% cotton; tea on a cotton-polyesterblend; and wine on 100% cotton. The soiled swatches were purchased fromTest Fabrics, Inc., West Pittston, Pa. The exposure of the swatches tothe various chemistries took place in a washing device known as aTerg-o-tometer (United States Testing Co., Hoboken, N.J.). The deviceprovides 6 stainless steel 1 L beakers immersed in a temperaturecontrolled water bath which was held at 100° F. for a 20 minutewash/bleach cycle. Each beaker includes an overhead agitator whichrotates 180 degrees before reversing at a frequency of 100 hz. Each testsolution contained sufficient bicarbonate-carbonate buffer to produce apH of approximately 7+/−0.5 units for the 20 minute wash cycle.

After completing the 20 minute wash cycle the fabric samples wereremoved and immediately rinsed with cold synthetic 5 grain water until 5cycles of fills and rinses were complete. The swatches were then laidflat and dried overnight on white polyester-cotton towels beforereflectance readings were taken using a spectrophotometer, e.g., HunterColor Quest XE (reflectance) Spectrophotometer.

To determine the percent (%) soil removal (SR), e.g., bleaching ability,the reflectance of the fabric sample was measured on aspectrophotometer. The “L value” is a direct reading supplied by thespectrophotometer. L generally is indicative of broad visible spectrumreflectance, where a value of 100% would be absolute white. The % soilremoval is calculated from the difference between the initial (beforewashing) lightness (L) value and the final L value (after washing):SR=((L _(final) −L _(initial))/(96−L _(initial)))×100%

The results of the soil removal/bleaching test are shown in the tablebelow.

TABLE 22 POAA (Peroxyacetic 2- 5- 6- 11- Buffer Composition acid) SPOAASPOHA SPOHXA SPOUA PSOA Control SR (%) Tea on 100% 50 4 47 45 12 62 11cotton SR (%) Tea on cotton- 42 −2 46 45 10 65 4 poly blend SR (%) RedWine on 68 46 72 69 48 80 34 100% cotton

These results of the soil removal/bleaching test were also compared tothe POAA control. The results are shown in the table below.

TABLE 23 POAA Buffer (Peroxyacetic 2- 5- 6- 11- Control Compositionacid) SPOAA SPOHA SPOHXA SPOUA PSOA (BWC) SR (%) Tea on 0 −46 −3 −5 −3812 −39 100% cotton SR (%) Tea on 0 −44 3 2 −32 22 −39 cotton-poly blendSR (%) Red Wine 0 −22 4 1 −20 12 −34 on 100% cotton

FIG. 8 also graphically depicts these soil removal results relative tothe soil removal achieved with an equimolar amount of peroxyacetic acid.

As can be seen from these results, with respect to bleaching, only thePSOA, a mid-chain sulfonated peracid, produced a significant improvementover peroxyacetic acid. The other terminally sulfonated peracids testedresulted in only small improvements over peroxyacetic acid in somecases, and in most cases produced a negative effect relative toequimolar peroxyacetic acid.

Example 14 Coupling Ability Study

A study was performed to determine the coupling/hydrotropic propertiesof various sulfonated peracids in aqueous solutions. The ability of theselected peracids to couple octanoic acid was measured.

The following sulfonated peracids were tested: 2-Sulfoperoxyacetic acid(2-SPOAA); 5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoicacid (6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); andsulfonated peroleic acid product (PSOA). Twenty grams (20 g) of eachperacid solution was diluted into a beaker containing hydrogen peroxide.Each peracid dissolved completely, except for 11-SPOUA which dissolvedonly partially. To each of these solutions, 0.4 grams of 1-octanoic acidwas added. The octanoic acid initially floated to the tops of thesolutions. The solutions were then stirred for 5-10 minutes withmagnetic stir bars at 1,000 rpm. The solutions were then centrifuged for20 minutes at 3,000-5,000 rpm. The lower phase of each solution was thencollected. The lower phases were further clarified by filtration through0.45 micron syringe filters. All of the filtrates appeared clear andhomogenous. The filtered solutions were analyzed by liquidchromatography for 1-octaonic acid. The results are shown in the tablebelow.

TABLE 23 Solution 1-Octanoic acid (ppm) 2-SPOAA 160 5-SPOHA 230 6-SPOHXA240 11-SPOUA 890 PSOA 13,200

As can be seen from these results, the mid-chain sulfonated peracid,PSOA, showed a far greater coupling ability for coupling octanoic acidcompared to the other terminally sulfonated peracids tested. Themid-chain sulfonated PSOA had approximately a 1300% greater ability tocouple octanoic acid compared to the next closest sulfonated peracid,11-SPOUA.

Example 15 Contact Angle Study

A study was performed to measure the wetting properties of varioussulfonated peracids in aqueous solutions, by measuring the contact angleof the individual solution on different surfaces.

The following sulfonated peracids were tested: 2-Sulfoperoxyacetic acid(2-SPOAA); 5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoicacid (6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); andsulfonated peroleic acid product (PSOA).

A FTA32 Contact Angle Goniometer with image processing by FTA 32software was used to measure the contact angle. The contact angle wasmeasured on both stainless steel, and polypropylene surfaces. Theperacid concentrates shown in the table below were diluted 250 timeswith DI water. However, the 11-SPOUA was diluted 85 times with DI water,given the lower levels of peracid precursor in the formula.

TABLE 24 2- 5- 6- 11- Composition SPOAA SPOHA SPOHXA SPOUA PSOA ControlPeracid 0.38% 1.02% 0.97% 0.41% 1.27% NA Titrated

The table below shows the contact angle observed for the tested peracidson both stainless steel and polypropylene surfaces. The results shownare the average of at least three contact angle measurements.

TABLE 25 Contact Angle (degree) Solution Stainless Steel Polypropylene2-SPOAA 77 75 5-SPOHA 68 75 6-SPOHXA 77 84 11-SPOUA 72 77 PSOA 52 56Control 81 79

As can be seen from these results, only the mid-chain sulfonated PSOAhad a significantly lower contact angle on both surfaces tested,compared to the control. The PSOA had about a 36% lower contact anglethan the control on the stainless steel surface, and about a 29% lowercontact angle than the control on the polypropylene surface. Withoutwishing to be bound by any particular theory, it is thought that a lowercontact angle indicates a greater wetting ability, resulting in greaterdetergency.

Example 16 Antimicrobial Study

A study was performed to determine the antimicrobial efficacy of varioussulfonated peracids. Use solutions containing 100 ppm of the followingpersulfonated acids were tested: 2-sulfoperoxyacetic acid (2-SPOAA);5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoic acid(6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); and sulfonatedperoleic acid product (PSOA).

The use solutions were tested against Staphylococcus aureus ATCC 6538and Escherichia coli ATCC 11229. The following test procedure was used.First, 99 ml of the persulfonated acid to be tested was dispensed into a250 ml flask. The liquid was allowed to equilibrate to 25±1° C. Theliquid was then swirled in the flask and 1 ml of a 10¹⁰ CFU/ml of thetest bacteria was added to the beaker. After the desired exposure time,1 mL of the combined peracid/bacteria solution was removed from theflask. The removed solution was then placed in 9 mls of an appropriateneutralizer. The desired dilution was then plated and allowed toincubate at 35° C. for 48 hours. The plates are then read to determinethe reduction in microbial count. For this experiment, samples weretested over 90 seconds total exposure time, at 10 second intervals.

The results are shown in FIGS. 9 and 10. These figures show the ratiobetween the survivors (N) and the initial inoculum numbers (N0) at agive time point. For example, if the ratio of survivors (N) to theinitial inoculum numbers (N0) is 1.0, no antimicrobial activity isachieved. As the rate approaches zero, complete kill is achieved. FIG. 9graphically depicts the efficacy of the tested persulfonated acidsagainst Staphylococcus aureus at ambient temperature. As can be seenfrom this Figure, the mid-chain sulfonated PSOA had a significantlyhigher reduction in the population of S. aureus than the otherterminally sulfonated peracids tested, both initially (at 10 seconds),and over the course of the time tested.

FIG. 10 graphically depicts the efficacy of the tested persulfonatedacids against Escherichia coli at ambient temperature. As can be seenfrom this Figure, the mid-chain sulfonated PSOA had a significantlyhigher reduction in the population of E. coli at 90 seconds, compared tothe short chain, terminally sulfonated peracids tested. Thus, overall,it was observed that mid-chain sulfonated peracids are more effective atreducing populations of S. aureus, and E. coli.

Example 17 Combined Cleaning, Bleaching and Disinfecting Compositionsfor Textiles

Formula G was prepared using 44.90 weight percent hydrogen peroxide (50%active), 0.10 weight percent dipicolinic acid, 2.0 weight percentsulfuric acid, 5.00 weight percent propylene glycol. To theseingredients sulfonated oleic acid (SOA), linear alkylbenzene sulphonate(LAS), and 1-octanoic acid were added (or not) in the amounts providedbelow.

In the first series of examples, the only carboxylic acid present in theformulas is sulfonated oleic acid. Therefore, the only peracid that canform is the peroxy-sulfonated oleic acid (PSOA), so that when the totalperacid level is titrated the measured value will only reflect theamount of PSOA

SOA LAS Octanoic Acid Formula (weight %) (weight %) (weight %) G1 48 — —G7 24 24 — G22 6 42 —

After formulation, the Formula G compositions were allowed toequilibrate at 100° F. for 1 week and then titrated to determine theamount of PSOA. These examples demonstrate peracid formation in a singlecarboxylic acid system containing only the PSOA type of sulfonated oleicacid.

Formula % PSOA G1 4.4 G7 4.4 G22 2.6

In the second series of examples, there was a mixed peracid systemcontaining two peracids: peroxyoctanoic acid (POOA) andperoxy-sulfonated oleic acid (PSOA). A standard iodine/thiosulfatetitration is unable to distinguish between the two peracids, so thetitrated value is equal to the total peracid content, i.e. the sum ofthe two peracids. To uniquely identify the amount of each component, thePOOA levels were determined by HPLC. The total peracid levels were thendetermined by iodometric titration. By subtracting the amount ofthiosulfate needed to titrate the POOA from the total amount ofthiosulfate used, the amount of thiosulfate needed to titrate the PSOAcould be determined. From that value, the percent PSOA in theformulations could be obtained. The single example shown belowdemonstrates the formation of PSOA in a mixed peracid system, and isrepresentative for all other examples.

Formula % POOA % PSOA G10 8.8 4.5 Octanoic Acid Formula SOA (weight %)LAS (weight %) (weight %) G2 — 48 — G3 — — 48 G4 8 8 32 G5 8 32 8 G6 328 8 G8 24 — 24 G9 — 24 24 G10 16 16 16 G11 5 36 7 G12 5 20.5 22.5 G13 55 38 G14 15.33 15.33 17.33 G15 20.5 20.5 7 G16 25.67 10.17 12.17 G1710.17 25.67 12.17 G18 10.17 10.17 27.67 G19 36 5 7 G20 20.5 5 22.5 G21 244 2

After formulation, the Formula G compositions were allowed toequilibrate at 100° F. for 1 week. Upon conclusion of that time period,the samples were evaluated for stability by visual inspection. Resultsare provided in the table below and show a variety of useful formularycapabilities covering both gel and liquid compositions.

Stability Results:

TABLE 27 Sample Visual appearance G1 Gel-like, single phase G5 Gel-like,single phase G17 Gel-like, single phase G7 Clear-liquid, single phaseG12 Clear-liquid, single phase G15 Clear-liquid, single phase G10Clear-liquid, single phase G16 Clear-liquid, biphasic G18 Clear-liquid,biphasic G1 Clear-liquid, biphasic G3 Clear-liquid, biphasic

Formulations were single phase when they had a high LAS content, andyielded gel-like formulations with a favorable and stable high viscosity(Samples G1, G5, G17). Conversely, and as desired in other formulationswhere a liquid is desired, as the LAS concentration decreased,formulations produced a clear, isotropic liquid (Samples G7, G12, G15,and G10). However, as the amount of either the SOA or octanoic acidincreased, the formulations exhibited gross phase separation resultingin two clear phases (Samples G16, G18, G1, G3). A range of productphases are most desirable that yield a single, liquid, solid, or gelphase. One single phase liquid is most desirable for some applicationsrequiring automated dosing pumps, while single phase gels are mostfavorable for hand-feed or non-automated processes. Though the modes offormulation optimization limits differed (e.g., gel formation for highLAS systems and phase separation for excessive octanoic acid and SOA),if any one surfactant comprised more than 50% of the total surfactantlevel it prevented the formation of a clear, isotropic liquid; however,it could yield a single phase gel.

Color-Stability of Formula G Samples

The color of the different formulations was evaluated using aspectrophotometer (Color Quest XE, Hunter Associates Laboratory). TheCIE L*, a*, b* color space is a 3-dimensional rectangular color spacebased on the opponent-colors theory. For the L* (lightness) axis 0 isblack and 100 is white. For the a* (red-green) axis positive values arered, negative values are yellow and 0 is neutral. For the b*(blue-yellow) axis positive values are yellow; negative values are blueand 0 is neutral. All colors that can be visually perceived can beplotted in this L*, a*, b* rectangular color space.

TABLE 28 Initial Sample Color: Sample L* A* B* G3 94.28 −3.47 12.47 G485.45 −4.14 20.68 G10 87.63 −5.89 20.76 G6 65.13 −5.03 33.08 G7 82.05−4.8 60.75

The above initial color data show there was significant color variationbetween formulations, especially in regard to b*, the blue-yellow axis.Regardless of starting color, samples lightened in color over time,ultimately becoming almost colorless (see Sample G10 data belowcomparing initial color and color at equilibrium). There is no specificthreshold above which the b* value, i.e. a greater degree of yellow, isconsidered unacceptable. Formulations with a higher starting b* valuewill exhibit greater color changes during the equilibration period,which could be perceived as a sign of instability. Therefore, a lowerinitial b* value, exhibited in Formula G samples containing moreoctanoic acid, could be perceived as more preferred than a higherinitial b* value.

TABLE 29 Initial color compared to equilibrium color: Sample L* A* B*G10 Initial 87.63 −5.89 20.76 G10 Equilibrium 89.62 −2.41 3.02Bleaching and Detergency Evaluation:

The Formula G compositions were evaluated for bleaching and detergencyusing wash wheel performance data. A commercial 35 lb front loadingwashing machine (Huebsch model HX35PVXU60001) was used for the tests.The ability of the Formula G compositions to remove soil was determinedby washing artificially soiled fabric swatches. The pre-soiled swatcheswere purchased from a Test Fabrics, Inc. located in West Pittston, Pa.Polyester/cotton blend pillowcases weighing 24 pounds were used asballast.

The wash formula was programmed to run for 14 minutes at 40° C. using 60liters of 5 grain synthetic soft water. One hundred grams of eachFormula G sample was added to the machine per run and no additionalchemicals were added allowing the actual run pH to fluctuate to itsnatural level. In the instances where the Formula G samples were not asingle, isotropic phase, the solutions were mixed by inversion twice aday for the week prior to the test, and the entire two phase sample wasadded to the wash-wheel. After the wash step, there were threesubsequent rinse cycles and a final extract. After completing the entirecycle, the soil swatches were retrieved from the washer and allowed toair dry overnight at 70° F.

Percent soil removal was determined by measuring the reflectance of thefabric using a Color Quest XE spectrophotometer available from HunterAssociates Laboratory. The “L value” was a direct reading supplied bythe spectrophotometer. L value is generally indicative of broad visiblespectrum reflectance, where a value of 100% would be absolute white. Thepercent soil removal was calculated using the following formula:SR=((L _(final) −L _(initial))/(96−L _(initial))))*100%The average stain removal data is provided in the following table:

TABLE 30 Percent Stain Removal Sample Coffee PC Curry Tea Sum G2 8.5 9.78.7 26.9 G21 21.6 18.9 22.3 62.8 G22 21.7 22 21.6 65.3 G5 39.8 33.3 23.396.4 G10 53.9 50.9 37 141.8 G4 56.5 51.4 39.1 147 G3 50.9 46.8 35 132.7G6 49.6 41.2 28.9 119.7 G1 41.3 32.1 19 92.4

Though hydrogen peroxide alone acts as an oxidizing bleach, it is knownto have severely reduced effectiveness at low temperatures and acidicpH. When LAS is present as a sole surfactant in the Formula G2 sample,there is no peracid formation. In that formulation lacking peracid, anybleaching that occurs is due solely to hydrogen peroxide and the stainremoval was minimal (i.e., <10% for any single bleachable soilclassification in columns 2-4); cf., G2 and all other formulations ofTable 30. As the other components (SOA, octanoic acid) were added(Formulas G1, and G3-G22) and the amount of potential peracid increased,so too did the stain removal. As can be seen, the amount of octanoicacid is the most important contributor to bleachable stain removal, withthe bleachable stain removal values increasing as octanoic acidincreased and decreasing as octanoic acid decreased. To optimizebleaching, octanoic acid is optionally included in the composition in anamount of between about 0.1 to 35 weight %, and between 2.0 and 25weight %; and between 4.0 weight % and about 20 weight %.

Detergency, or removal of soils that were not susceptible to oxidation,was also evaluated. Detergency results are provided below:

TABLE 31 Percent Stain Removal Sample Olive Oil PC Lipstick Makeup SumG2 21.2 62.5 18.9 102.6 G21 22.6 53.3 18.1 94 G22 21.7 64.6 22.3 108.6G5 27.2 68.1 21 116.3 G10 28.9 66.9 26.2 122 G6 21.8 67.7 28.7 118.2 G418.3 66.5 23.6 108.4 G1 26.8 66 31.1 123.9 G3 17 65.6 20.3 102.9

Detergency was less dependent upon formulation than bleaching exceptwhen formulations had high (or exclusive) LAS and octanoic acid. Theresults suggest that the presence of multiple surfactants can bebeneficial although the exact ratio of the surfactants doesn't seem tocause significant differences in results. Most importantly this widevariance in formulation capability allows for preparation ofcompositions that are liquids, gels, or solids.

pH

As already mentioned, the pH of the use solution was allowed to vary toits natural level, i.e. no additional chemicals were added to target acertain pH throughout the wash tests. After the formulations weredispensed into the washwheel, they were allowed to mix for one minuteafter which a 100 mL aliquot was removed and the pH measured. The pHmeasurements are provided below:

TABLE 32 Sample pH G1 6.2 G10 5.8 G6 5.9 G16 6 G14 3.9 G10 6.7 G15 4.4G12 2.6 G7 3.3 G17 2.9 G1 2.8

Peracids are weaker acids (that is, have a higher pKa value) than theparent carboxylic acid. Greater peracid formation in the concentrateshould lead to a higher pH with the use solution; especially in thepresence of typical water hardness conditions found in many textilelaundering waters. Since LAS is unable to form a peracid, it remains inits most acidic form. Given the above, formulations containing higheramounts of LAS and lower peracid conversion will have a lower pH in thewash-wheel. Greater amounts of SOA and octanoic acid yield a higher pHupon dilution and may be more preferred in textile applications.

Example 18 Combined Cleaning, Bleaching and Disinfecting Compositionsfor Textiles with Varied Nonionic, Amine Oxide, and Anionic Surfactantsand Amounts

Formula H was prepared using 13 weight % sulfonated oleic acid, 35.9weight % hydrogen peroxide, 13 weight % alkyl (C₁₀-C₁₆) benzenesulfonicacid, 13 weight % 1-octanoic acid, 0.1 weight %pyridine-2,6-dicarboxylic acid. To the Formula H compositions, theingredients provided in the following tables were added in the amountsprovided to prepare Formula H samples H1-H25. The initial stability dataof the Formula H samples was indicated.

TABLE 33 Sample Ingredient H1 H2 H3 H4 H5 H6 H7 Sulfuric Acid 1.5 1.51.5 1.5 1.5 1.5 1.5 Propylene glycol 23.5 3.5 3.5 3.5 3.5 3.5 3.5Benzenesulfonic 0 0 0 5 0 0 5 acid Primary C₁₂-C₁₄ 0 20 10 10 10 0 0linear alcohol plus 7 ethylene oxide (EO) groups Primary C₁₂-C₁₄ 0 0 105 0 0 0 linear alcohol plus 3 EO groups Primary C₁₂-C₁₄ 0 0 0 0 20 0 0linear alcohol plus 12 EO groups Branched C₁₃ 0 0 0 0 0 20 15 alcoholplus 7 EO groups C₁₀ Guerbet 0 0 0 0 0 0 0 alcohol alkoxylate plus 5 EOgroups Nonionic seed oil 0 0 0 0 0 0 0 surfactant (Ecosurf SA-4)Nonionic seed oil 0 0 0 0 0 0 0 surfactant (Ecosurf SA-9)Benzenesulfonic 0 0 0 0 0 0 0 acid Lauryl dimethyl 0 0 0 0 0 0 0 amineoxide Citric acid 0 0 0 0 0 0 0 Alkyl 0 0 0 0 0 0 0 polyglucoside basedon natural fatty alcohol C₈-C₁₆ Polyoxyethylene 0 0 0 0 0 0 0 sorbitanmonolaurate Succinic Acid 0 0 0 0 0 0 0 Acrylic acid 0 0 0 0 0 0 0homopolymer, Avg. MW 4500 Acrylic/maleic 0 0 0 0 0 0 0 copolymer4,4′-Bis(2- 0 0 0 0 0 0 0 sulfostryl)biphenyl disodium salt1-hydroxyethane 0 0 0 0 0 0 0 1,1-diphosphonic acid 2,6-diterbutyl-4- 00 0 0 0 0 0 methylphenol Coconut oil fatty 0 0 0 0 0 0 0 acid Siliconeantifoam 0 0 0 0 0 0 0 emulsion Magnesium 0 0 0 0 0 0 0 sulfateStability Data Clear, Clear, Cloudy Clear, Clear, Cloudy, Clear, singlesingle biphasic single single single single phase phase phase phasephase phase Sample Ingredient H8 H9 H10 H11 H12 H13 H14 Sulfuric Acid1.5 1.5 1.5 1.5 1.5 0 0 Propylene glycol 3.5 3.5 3.5 3.5 3.5 5 5Benzenesulfonic 5 0 5 0 5 0 0 acid Primary C₁₂-C₁₄ 0 0 0 0 0 0 0 linearalcohol plus 7 ethylene oxide (EO) groups Primary C₁₂-C₁₄ 0 0 0 0 0 0 0linear alcohol plus 3 EO groups Primary C₁₂-C₁₄ 0 0 0 0 0 0 0 linearalcohol plus 12 EO groups Branched C₁₃ 0 0 0 0 0 5 0 alcohol plus 7 EOgroups C₁₀ Guerbet 20 15 0 0 0 0 0 alcohol alkoxylate plus 5 EO groupsNonionic seed oil 0 0 5 0 0 0 0 surfactant (Ecosurf SA-4) Nonionic seedoil 0 0 10 0 0 0 0 surfactant (Ecosurf SA-9) Benzenesulfonic 0 0 0 0 5 00 acid Lauryl dimethyl 0 0 0 20 15 0 0 amine oxide Citric acid 0 0 0 0 010 10 Alkyl 0 0 0 0 0 5 0 polyglucoside based on natural fatty alcoholC₈-C₁₆ Polyoxyethylene 0 0 0 0 0 0 10 sorbitan monolaurate Succinic Acid0 0 0 0 0 0 0 Acrylic acid 0 0 0 0 0 0 0 homopolymer, Avg. MW 4500Acrylic/maleic 0 0 0 0 0 0 0 copolymer 4,4′-Bis(2- 0 0 0 0 0 0 0sulfostryl)biphenyl disodium salt 1-hydroxyethane 0 0 0 0 0 0 01,1-diphosphonic acid 2,6-diterbutyl-4- 0 0 0 0 0 0 0 methylphenolCoconut oil fatty 0 0 0 0 0 0 0 acid Silicone antifoam 0 0 0 0 0 0 0emulsion Magnesium 0 0 0 0 0 0 0 sulfate Stability Data Cloudy Clear,Clear, Clear, Clear, Clear, Clear, biphasic single single biphasicsingle single single phase phase phase phase phase Sample Ingredient H15H16 H17 H18 H19 H20 H21 Sulfuric Acid 1.5 1.5 1.5 1.5 1.5 1.5 1.5Propylene glycol 3.5 3.5 18.5 18.5 23.2 18.5 21.5 Benzenesulfonic 0 0 00 0 0 0 acid Primary C₁₂-C₁₄ 0 0 0 0 0 0 0 linear alcohol plus 7ethylene oxide (EO) groups Primary C₁₂-C₁₄ 0 0 0 0 0 0 0 linear alcoholplus 3 EO groups Primary C₁₂-C₁₄ 0 0 0 0 0 0 0 linear alcohol plus 12 EOgroups Branched C₁₃ 0 0 0 0 0 0 0 alcohol plus 7 EO groups C₁₀ Guerbet 00 0 0 0 0 0 alcohol alkoxylate plus 5 EO groups Nonionic seed oil 0 0 00 0 0 0 surfactant (Ecosurf SA-4) Nonionic seed oil 0 0 0 0 0 0 0surfactant (Ecosurf SA-9) Benzenesulfonic 0 0 0 0 0 0 0 acid Lauryldimethyl 0 0 0 0 0 0 0 amine oxide Citric acid 20 0 0 0 0 0 0 Alkyl 0 00 0 0 0 0 polyglucoside based on natural fatty alcohol C₈-C₁₆Polyoxyethylene 0 0 0 0 0 0 0 sorbitan monolaurate Succinic Acid 0 20 00 0 0 0 Acrylic acid 0 0 5 0 0 0 0 homopolymer, Avg. MW 4500Acrylic/maleic 0 0 0 5 0 0 0 copolymer 4,4′-Bis(2- 0 0 0 0 0.3 0 0sulfostryl)biphenyl disodium salt 1-hydroxyethane 0 0 0 0 0 5 01,1-diphosphonic acid 2,6-diterbutyl-4- 0 0 0 0 0 0 2 methylphenolCoconut oil fatty 0 0 0 0 0 0 0 acid Silicone antifoam 0 0 0 0 0 0 0emulsion Magnesium 0 0 0 0 0 0 0 sulfate Stability Data Clear, Cloudy,Clear, Cloudy, Clear, Clear, Clear, single biphasic one single singlesingle single phase phase phase phase phase phase Ingredient H22 H23 H24H25 Sulfuric Acid 1.5 1.5 1.5 1.5 Propylene glycol 13.5 1.5 1.5 1.5Benzenesulfonic 0 0 0 0 acid Primary C₁₂-C₁₄ 0 0 0 0 linear alcohol plus7 ethylene oxide (EO) groups Primary C₁₂-C₁₄ 0 0 0 0 linear alcohol plus3 EO groups Primary C₁₂-C₁₄ 0 0 0 0 linear alcohol plus 12 EO groupsBranched C₁₃ 0 0 0 0 alcohol plus 7 EO groups C₁₀ Guerbet 0 0 0 0alcohol alkoxylate plus 5 EO groups Nonionic seed oil 0 0 0 0 surfactant(Ecosurf SA-4) Nonionic seed oil 0 0 0 0 surfactant (Ecosurf SA-9)Benzenesulfonic 0 0 0 0 acid Lauryl dimethyl 0 0 0 0 amine oxide Citricacid 0 0 0 0 Alkyl 0 0 0 0 polyglucoside based on natural fatty alcoholC₈-C₁₆ Polyoxyethylene 0 0 0 0 sorbitan monolaurate Succinic Acid 0 0 00 Acrylic acid 0 0 0 0 homopolymer, Avg. MW 4500 Acrylic/maleic 0 0 0 0copolymer 4,4′-Bis(2- 0 0 0 0 sulfostryl)biphenyl disodium salt1-hydroxyethane 0 0 0 0 1,1-diphosphonic acid 2,6-diterbutyl-4- 0 0 0 0methylphenol Coconut oil fatty 10 10 0 0 acid Silicone antifoam 0 0 0.20 emulsion Magnesium 0 0 0 5 sulfate Stability Data Clear, Clear, Clear,Clear, single single biphasic biphasic phase phase

As evident from the data, not all of the Formula H Samples wereimmediately stable after addition of the various nonionic, amine oxide,or anionic surfactants. In each of those instances, the sample could bemade stable by the addition of a small amount of a classic hydrotrope,such as 5 weight percent sodium cumene sulfonate, and, thus, extend theliquid, gel, and solid formulation scope for the current invention.

Detergency of the Samples H1-H25 was tested and no significantdifferences in detergency resulted between any of the samples; thusshowing the wide scope of formulations capable of enabling the currentinvention. Laundry compositions as prepared in the Formula G and Hsamples were effective at cleaning, bleaching, and disinfecting despitethe absence of nitrogen-based chelants, phosphorous and/or phosphatesand/or phosphonates, and heavy metal—specifically transition metals,post-transition metals, and metalloids with an atomic number above 38.These examples also demonstrate systems free of caustic or alkali metalhydroxide in the compositions; however, other systems using caustic oralkali metal hydroxides to moderate the pH to various desirable levelsare also disclosed in other example of the current application.

Example 19 Extended Peracid Stability of Combined Cleaning, Bleachingand Sanitizing and/or Disinfecting and/or Sterilizing Compositions

In these combined detergent, bleach and/or antimicrobial compositions,the bleaching and/or antimicrobial effect is a result of the peracidformed through an acid reaction. One requirement for aperacid-containing product is long term stability where the peraciddoesn't rapidly decompose or revert back to the starting carboxylicacid. Shown in Table 34 is a wide variety of formulations containingdifferent types of raw materials, including surfactants, solvents orcosolvents and antifoam agents. As a means of accelerating testing, thesamples are usually stored at elevated temperatures, in this case 100°F.

TABLE 34 I1 I2 I3 I4 I5 I6 Sulfonated oleic acid 16 12 12 6.3 12 12Hydrogen peroxide 44.9 33.9 33.9 18 33.9 33.9 (50%) Alkyl (C10-C16) 1612 6 6.3 6 6 Benzenesulfonic acid 1-Octanoic acid 16 12 12 6.3 12 12pyridine-2,6- 0.1 0.1 0.1 0.1 0.1 0.1 dicarboxylic acid Sulfuric acid 2propylene glycol 5 5 5 10 5 5 Primary C12-C14 25 31 53 21 29 linearalcohol plus 7 ethylene oxide (EO) groups Coconut oil fatty acid 10Aluminum sulfate 2 Sum 100 100 100 100 100 100

In all cases the peracid level remained relatively constant over time,showing only minimal degradation from initial formation to day 28 (Table35). In some examples with lesser amounts of acid, it takes some timefor the peracid to reach a reaction level. In formulas I1 and I2 thereaction level is reached rapidly, as demonstrated by the minimal changebetween Day 0 and Day 4. Formulas I3, I4, I5, and I6 all have lowerlevels of LAS, the strongest acid present in those formulas. This leadsto slower equilibrium or reaction level peracid formation, asdemonstrated by the peracid levels increasing between Day 0 and Day 4,in some instances by almost 100%. Regardless of the initial rate ofperacid formation, the stability over time is unaffected.

TABLE 35 % Peracid Day 0 Day 4 Day 7 Day 28 I1 11.0 10.9 10.8 10.6 I26.8 6.9 6.5 6.0 I3 3.8 6.1 5.6 5.3 I4 1.9 3.2 2.9 2.0 I5 4.5 8.9 8.7 7.1I6 4.0 6.1 6.3 5.9

Example 20 Foam Levels from Combined Cleaning, Bleaching and/orSanitizing Compositions

Foam control is an important priority for all laundry detergents, butespecially when used in front loading washer extractors, or continuousbatch (tunnel) washers. These two types are the predominant washersfound in industrial and institutional laundries. Too much foam canimpede the wash process by reducing soil removal and interfering witheffective rinsing. To mimic the amount of foam that is generated duringactual washer usage, a laboratory method may be used. A small amount(0.25 g) of the test sample was added to 100 g of soft (0 grain) waterin a 250 mL graduated cylinder. The cylinder was stopped and thenagitated through 120 degree rotations for 1 minute (about 1 cycle/sec).After agitation the foam was allowed to settle for 1 min, and the totalvolume was measured. The volume of the foam was equal to the totalvolume minus the initial water volume (100 mL). The formulations testedare seen in Table 36. L2000 XP is an institutional laundry detergentcommercially available from Ecolab, Inc. The data is reported as foamvolume (mL), normalized per g of material (Table 37).

TABLE 36 J1 J2 J3 J4 J5 J6 J7 J8 Sulfonated 12 12 12 12 12 12 12 12oleic acid Hydrogen 33.9 33.9 33.9 33.9 33.9 34.9 35.9 35.9 peroxide(50%) Alkyl 6 6 6 6 6 6 4 4 (C10-C16) Benzene- sulfonic acid 1-Octanoicacid 12 12 12 12 12 12 12 12 pyridine-2, 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.16-dicarboxylic acid propylene 5 5 5 5 5 13 5 5 glycol Primary 31 28 2128 21 20 28.5 26 C12-C14 linear alcohol plus 7 ethylene oxide (EO)groups Lauric acid 3 10 Coconut oil 3 10 fatty acid Aluminum 2 sulfatePrimary 2.5 5 C9-C11 linear alcohol plus 20 propylene oxide (PO) groupsSum 100 100 100 100 100 100 100 100

TABLE 37 Foam volume (mL)/g Formula sample L2000 XP 351 J1 516 J2 468 J3296 J4 560 J5 339 J6 475 J7 461 J8 373

The commercially available detergent, L2000 XP, has a foam volume of 351mL/g. The initial experimental formula (J1) produced more foam than thecommercial standard with a volume of 516 mL/g. Addition of a long chainfatty acid (lauric acid, J2 and J3) reduces the foam volume compared tothe original formula without lauric acid. It also shows a dose responserelationship with 3% lauric acid (J2) reducing the foam by 9.3% and 10%lauric acid (J3) reducing the foam volume by 42.6%. With thatsignificant reduction, the foam volume from Formula J3 is less than thecommercially available reference detergent, L2000 XP. Similar to thefoam reduction seen with the long chain fatty acids, an alcoholalkoxylate with extended propylene oxide groups also saw significantreductions. Adding 2.5% of the alcohol alkoxylate (J7) reduced the foamby 10.7%. Doubling the alkoxylate to 5% of the formulation (J8), broughtthe total foam reduction to 27.7%, and the absolute foam level into therange of the commercial detergent L2000 XP.

Example 21 Mineral Encrustation after Washing

Hardness is a measure of the calcium and magnesium ions present inwater. These ions can precipitate out of solution as the carbonate form,i.e. calcium carbonate, and can deposit on surfaces. This process isaccelerated under alkaline washing conditions, especially the morehighly alkaline conditions often employed in industrial andinstitutional cleaning. Controlling encrustation is therefore requiredfor alkaline laundering.

To assess the encrustation levels, one of the experimental formulationswas compared to Formula 1, a commercially available detergent fromEcolab. For each condition six new 100% cotton terry towels wereselected. Additional towels were added to bring the total weight to 28lbs. Prior to the start of the test (Cycle 0) and after every 5 cycles(i.e. 5, 10, 15 and 20) three circles that summed to 10 g were removedfrom each of the 6 test towels. The cycles were run using 17 grain waterand the towels were dried after each cycle. After completion of thetest, all sets of towel pieces were heated in an oven at 600° F. for 12hours, and cooled to room temperature. The beakers were weighed and thedifference in final mass compared to the initial mass is the mass of theinorganic residue, or ash. Dividing that number by the starting mass ofthe towels, i.e. 10 g, gives the ash percent. The amount of ash is ameasure of the mineral encrustation deposited on the towels. The resultsare seen in Table 38.

TABLE 38 Ash Percent Cycle Formula 1 I6 0 0.22 0.25 5 0.29 0.26 10 0.410.29 15 0.55 0.30 20 0.77 0.32Each system had some level of inorganic residue present at the start ofthe test and both saw increasing levels of ash content throughout the 20cycles. The Formula 1 ash content had an increase of 250%. By contrast,the formulation of the present invention only increased by 28%. Withoutwishing to be bound by theory it is believed that the acidic washingconditions of the present invention inhibit significant calciumcarbonate precipitation, a favorable benefit in comparison to alkalinelaundering.

Example 22 pH Adjustment of Combined Cleaning, Bleaching and/orAntimicrobial Compositions

In most instances the pH of the concentrated compositions is between0-1. In some examples it may be beneficial to raise the pH of theconcentrate product above 1. To do so, a batch was created and allowedto sit overnight to afford peracid formation, after which various baseswere added until the desired pH was reached. The pre-neutralization baseformula seen in Table 38 is used in all of the subsequent pH-adjustmentexamples. A product concentrate pH range from 0-4.5 is demonstrated. Theabsolute upper limit of the range is not established herein, and pHvalues higher than pH 4.5 are envisioned to be within the scope of thepatent. After neutralization, the compositions were stored at 104° F.,an accelerated aging condition compared to room temperature.

TABLE 39 K Sulfonated oleic acid 35 Hydrogen peroxide (50%) 20 Alkyl(C10-C16) Benzenesulfonic 10 acid pyridine-2,6-dicarboxylic acid 0.1propylene glycol 5 Primary C12-C14 linear alcohol 29.9 plus 7 ethyleneoxide (EO) groups Sum 100

Different amounts of each base listed in Table 40 were added to raisethe concentrate pH from the starting value (pH≦1) up to the Day 0 valueseen in the first column. After the initial adjustment, some samplesshow moderate pH fluctuation over time, whereas other samples only showminimal pH fluctuation over time. The samples where the pH was adjustedwith sodium hydroxide are examples of the overall trend. Immediatelyafter neutralization there is a sharp decline in titrated peracidlevels, demonstrated by the change from day 0 to day 7. However, afterthat initial drop it appears that a new reaction level is reached andfor the remainder of the observation period the peracid levels stayrelatively constant (compare day 7 to day 28 for all 3 of the sodiumhydroxide samples.) Though the initial drop is not captured, this sameperiod of peracid stability is demonstrated with the other bases aswell. A second series of base additions can be seen in Table 41.

TABLE 40 pH % Peracid Base Day 0 Day 28 Day 0 Day 7 Day 14 Day 21 Day 28Sodium Hydroxide 2.6 2.2 4.0 1.9 1.4 — 2.1 Sodium Hydroxide 3.0 2.3 3.82.4 2.1 — 2.2 Sodium Hydroxide 3.5 2.3 4.0 1.5 1.2 — 1.6 Sodium silicate2.5 1.7 — — 2.4 1.6 1.8 Sodium silicate 3.5 2.2 — — 1.3 2.0 2.0Potassium hydroxide 2.6 2.4 — 1.3 1.0 — 1.6 Potassium hydroxide 4.5 2.8— 1.1 1.1 — 1.2

TABLE 41 pH % Peracid Base Day 0 Day 28 Day 0 Day 7 Day 14 Day 21 Day 28Sodium carbonate 2.5 2.5 — — 1.8 2 1.8 Sodium bicarbonate 2.5 1.5 — —3.3 3.3 3.2 Sodium silicate 2.5 1.7 — — 2.4 1.6 1.8 Sodium metasilicate2.5 2 — — 2.4 2.6 2.6 Potassium hydroxide 2.6 2.4 — 1.3 1.0 — 1.6 Sodiumglutarate 2.5 2.2 — 1.9 1.6 — 1.5

As with the first series of base additions, after the initial adjustmentthere are some examples that show pH fluctuation over time, and otherexamples that do not. Another similarity between the two series of baseadditions is the period of peracid stability after the initial drop.This period of stability is demonstrated by comparing the earliesttitration values (either day 7 or day 14) with the latest measurement(day 28). The above data demonstrates relatively little change betweenthose two time points, again suggesting that a new reaction level isreached after the initial pH adjustment.

Example 23 pH Adjustment of Combined Cleaning, Bleaching and/orAntimicrobial Compositions, Mixed Peracid System

The formula studied in example 22 (Table 39) contained only a singleperacid, PSOA. In some instances it may be desirable to use acomposition containing multiple peracids. Therefore, the neutralizationof a composition containing two peracids (POOA and PSOA) was alsostudied (Table 42).

TABLE 42 Formula L Sulfonated oleic acid 20 1-Octanoic acid 4 Hydrogenperoxide (50%) 20 Alkyl (C10-C16) Benzenesulfonic 6 acidpyridine-2,6-dicarboxylic acid 0.1 propylene glycol 5 Sodium cumenesulfonate 15 Primary C12-C14 linear alcohol 29.9 plus 7 ethylene oxide(EO) groups Sum 100As in the earlier example, the various bases listed in Table 43 wereeach added to Formula L. With this two peracid system similar trends toa single peracid system were noticed. Immediately after neutralizationthere was a drop in peracid levels. However, in all systems tested thelevel did not drop significantly from day 7 to day 28. Like the singleperacid systems, when sodium carbonate or sodium bicarbonate was used asthe neutralizing base the peracid level stayed essentially constant overtime. By contrast, with all hydroxide bases tested the peracid levelsactually rose from day 7 to day 28.

TABLE 43 pH % Peracid Base Day 0 Day 28 Day 0 Day 7 Day 14 Day 21 Day 28Lithium hydroxide 2.1 2.4 4.9 2.6 3.2 3.3 3.5 Sodium hydroxide 2.0 1.95.2 2.5 2.6 3.2 3.6 Potassium hydroxide 2.3 1.9 4.9 2.6 2.8 3.1 3.4Sodium carbonate 2.5 2.3 6.3 4.8 4.3 — 4.1 Sodium bicarbonate 2.7 2.46.1 4.4 4.4 — 4.0To show broad scope formulation capability, another composition wascreated with higher levels of octanoic acid. The higher absolute peracidlevels are a reflection of the lower molecular weight of octanoic acidcompared to sulfonated oleic acid, meaning there are more starting molesof carboxylic acid that can be converted to the percarboxylic acid.Given that, it is apparent that the final peracid level can be varied byadjusting the amount of starting carboxylic acids. Similarly to thecomposition containing a lesser amount of octanoic acid (Formula L),Formula M saw a sharp drop in peracid levels immediately afterneutralization. Again, after the initial drop the peracid levels did notdecrease significantly from day 7 to day 28.

TABLE 44 Formula M Sulfonated oleic acid 12 1-Octanoic acid 12 Hydrogenperoxide (50%) 20 Alkyl (C10-C16) Benzenesulfonic 6 acidpyridine-2,6-dicarboxylic acid 0.1 propylene glycol 5 Sodium cumenesulfonate 20 Primary C12-C14 linear alcohol 24.9 plus 7 ethylene oxide(EO) groups Sum 100

TABLE 45 pH % Peracid Base Day 0 Day 28 Day 0 Day 7 Day 14 Day 21 Day 28Lithium hydroxide 4.0 1.7 11.3 6.6 6.0 6.1 6.5 Sodium hydroxide 2.0 1.510.9 7.5 7.2 6.7 7.0 Potassium hydroxide 2.1 1.5 10.8 7.4 7.0 7.2 7.3Sodium carbonate 2.7 2.1 12.1 9.5 8.1 — 7.6 Sodium bicarbonate 2.9 2.212.0 8.2 7.9 — 8.2

Synthesis of Selected Compounds of the Invention

Preparation of the Sulfonated Peroleic Acid Product.

417.8 g of OA5-R (Intertrade Organic's, 40% active Sulfonated Oleicacid) was added to a 2-L beaker immersed in a large ice-bath, to whichwas subsequently added, 66.4 g of Dequest 2010 (60% activeHydroxyethylenediphosphonic acid, Monsanto) and 535 g of Hydrogenperoxide (46% active, Solvay-Interox). The beaker was fitted with amagnetic stir bar and the solution was stirred aggressively while adding940 g of sulfuric acid (96% active, Mallinkrodt). The rate of thesulfuric acid addition was controlled to produce a 120° F. exotherm inthe reaction solution, and while this was occasionally exceeded byseveral degrees F., it wasn't allowed to exceed 125° F. Several minutesafter completing the sulfuric acid addition, the ice bath was removedand the heterogenous solution was stirred for 72 hours allowing thetemperature to equilibrate to ambient (70° F.) conditions.

Several hours after discontinuing the stirring, the two phase reactionsolution was added to a separatory funnel and the upper and lower phasewere separated. 239.4 g of upper phase were collected and the upperphase was further purified by centrifugation at 3000 rpm for 10 minutes.The final upper phase yield was 206 g and titrated as 60% Peroxyacidbased upon an assumed molecular weight of 412 (theoretical yield 178 g).In addition the upper phase contained 1.8% Hydrogen peroxide. Acentrifuged lower phase sample titrated as 14% Peroxyacid (MW 412) and8.8% hydrogen peroxide.

Synthesis of 11—Sulfoundecanoic Acid and 10,11-Disulfoundecanoic Acid

11-Sulfoundecanoic Acid

Deionized water (150 ml), isopropyl alcohol (200 ml) and 11-undecylenicacid (28.56 g, 0.155 mol) were placed in a 1.0 liter flask equipped withstirrer, additional funnel, reflux condenser, thermometer and a gasinlet tube. To the additional funnel was added a premix which contained15.2 g (0.08 mol) of sodium metabisulfite and 1.28 g of NaOH in 55 g ofwater. The whole device was purged with nitrogen gently. After heatingto reflux (82° C.), a small portion of t-butyl perbenzoate (out of totalamount of 0.5 g, 2.5 mmol) was added to the flask. Then the sodiummetabisulfite/NaOH premix was added continuously over a five hour periodto the reaction solution through an addition funnel. The remainingt-butyl perbenzoate was also added in small portions during this time.

The solvent was then removed under reduced pressure using a rotavapour,and the residue washed with acetone, and dried, yielding 31.0 g of whitesolid. NMR analysis of the solid indicated no presence of the residualraw materials. The white solid obtained was dissolved in hot water (100ml, 75° C.), and neutralized to pH 5.5 with NaOH. Then 2.0 g of 50% H₂O₂was added to the solution. The solution was then allowed to cool down toroom temperature, and the solid precipitated was filtered, washed withcold water, and dried, affording 21.0 g of white solid, characterized aspure 11-sulfoundecanoic acid. ¹³C NMR (D₂O): 180, 51, 34, 28-29(multiple), 27.5, 24.5, 24 ppm. MS (ESI): 265.1 (M′-H).

10,11-Disulfoundecanoic Acid

this compound was obtained as a byproduct from the 11-Sulfoundecanoicacid reaction as described above. The filtrate, after collecting11-sulfoundecanoic acid through filtration, was concentrated to ˜50 mlwhen precipitate start to form. The mixture was cooled down in therefrigerator, and the additional solid formed was filtered, washed witha small amount of ice water, and dried, yielding 5.0 g of white solid.¹³C NMR (D₂O): 184, 57, 51.5, 37.5, 28-29 (multiple), 27.5, 26, 24 ppm.MS (ESI): 345.0.

Synthesis of 11—Sulfoundecaneperoxoic acid (Compound D) and10,11-Disulfoundecaneperoxoic acid (Compound E) 11-SulfoperoxyundecanoicAcid

1.3 g of 11-sulfoundecanoic acid was dissolved in 2.5 g of 98% sulfuricacid. To this solution (the temperature of the solution did not exceed60° C.) 1.5 g of 50% H₂O₂ was added, and the resulting mixture wasstirred at room temperature for 1.5 hr. At this point, a white solidprecipitated from the solution. The mixture was reheated to 50° C. witha water bath until the solution was clear. The solution was then stirredat room temperature for 0.5 hr, and cooled down in the freezer. Then 20ml of ice water was added to the mixture, and the solid filtered, washedwith ice water, and dried under vacuum, yielding 0.6 g of a white solid.¹³C NMR (D₂O): 176, 51.5, 30.5, 27.5-29 (multiple), 24.5, 24 ppm. MS(ESI): 281.5 (M⁺-H). Available oxygen (iodometric): 5.41% (theoretical:5.64%).

10,11-Disulfoundecaneperoxoic Acid (Compound E)

To 1.5 g of 10,11-disulfoundecanoic acid was added 2.5 g of 96% H₂SO₄,and the mixture was stirred at room temperature. Then 1.0 g of 50% H₂O₂was added slowly (the temperature not exceeding 60° C.) to the mixture,and after addition, the mixture was heated to 50° C. with water bath,and the solution stirred for 2.0 hrs. The solution was then cooled downin the freezer, and 20 ml of ice water was added with stirring. Thesolid precipitated was filtered, washed with ice water, and dried undervacuum, affording 1.0 g of white solid. ¹³C NMR (D₂O): 175.5, 57, 30.5,27.5-29 (multiple), 24.5, 24 ppm. Available oxygen (iodometric): 4.10%(theoretical: 4.41%).

Synthesis of 9/10-Sulfostearic Acid (Sulfonated Stearic Acid)

Deionized water (150 ml), isopropyl alcohol (200 ml) and oleic acid(43.78 g, 0.155 mol) were placed in a 1.0 liter flask equipped withstirrer, additional funnel, reflux condenser, thermometer and a gasinlet tube. To the additional funnel was added a premix which contained15.2 g (0.08 mol) of sodium metabisulfite (Na₂S₂O₅) and 1.28 g of NaOHin 55 g of water. The whole device was bubbled gently with nitrogen.After heating to reflux (82° C.), a small portion of t-butyl perbenzoate(out of total amount of 0.5 g, 2.5 mmol) was added to the flask. Thenthe Na₂S₂O₅/NaOH premix was added through the addition funnelcontinuously over the course of five hours. The remaining t-butylperbenzoate was also added in portions during this time.

The solvent was then removed under reduced pressure using rotavapour. Tothe residue was added 100 ml of DI water, the pH of the solution wasadjusted to 2.5 with H₂SO₄. The resulting mixture/solution wastransferred to a separation funnel, and the top oily layer (non reactedoleic acid) was removed. The aqueous layer was extracted with petroleumether (2×50 ml), and after removal of the water, afforded 12.5 g ofwhite waxy solid. ¹³C NMR (D₂O): 179, 60, 34.5, 32, 28.5-30 (multiple),24.5, 22.5, 14 ppm. MS (ESI): 363.4 (M⁺-H).

Preparation of 9/10-Sulfoperoxystearic Acid (in formulation)

To a 2.0 g mixture of 9 or 10-Sulfostearic acid was added 2.0 g of 50%H₂O₂. The mixture was stirred at room temperature until all the solidwas dissolved. Then, 2.0 g of 75% H₃PO₄ was added, and the resultingsolution was stirred at room temperature overnight. No attempt was madeto isolate the pure 9 or 10-sulfoperoxystearic acid from solution. ¹³CNMR (D₂O) of the solution showed a peracid peak (COOOH) at 174 ppm andthe parent the carboxylic acid peak at 178 ppm. The iodometric titration(QATM-202) indicated 18.96% of sulfoperoxystearic acid.

The invention claimed is:
 1. A laundry composition, comprising: acompound according to Formula I:

wherein: R₁ is a substituted or unsubstituted C_(m) alkyl group, R₂ is asubstituted or unsubstituted C_(n) alkylene group, X is hydrogen, acationic group, or an ester forming moiety, n is 1 to 10, m is 1 to 10,and m+n is less than or equal to 18, or salts, esters, or mixturesthereof; wherein the composition includes a mixture of10-hydroxy-9-sulfooctadecaneperoxoic acid;10,11-dihydroxy-9-sulfooctadecaneperoxoic acid;9-hydroxy-10-sulfooctadecaneperoxoic acid; and10-sulfo-8,9-dihydroxyoctadecaneperoxoic acid; and oxidizing agent;surfactant; carboxylic acid; and stabilizing agent.
 2. The compositionof claim 1 further comprising a viscosity reducer.
 3. The composition ofclaim 1 further comprising a defoamer.
 4. The composition of claim 3wherein the defoamer is an alkyl alkoxylate containing in part or wholepoly-propylene oxide units.
 5. The composition of claim 1 wherein thecomposition is a liquid, gel or solid.
 6. The composition of claim 1,wherein the pH of the composition is less than about
 7. 7. Thecomposition of claim 1, wherein the compound is present at about 0.05 wt% to about 50 wt %.
 8. The composition of claim 1, wherein the compoundis present at about 0.05 wt % to about 30 wt %.
 9. The composition ofclaim 1, wherein the compound is present at about 1.0 wt % to about 20wt %.
 10. The composition of claim 1, wherein the compound is present atan effective antimicrobial amount.
 11. The composition of claim 9,wherein the compound is present in an amount effective for reducing apopulation of a bacteria selected from the group consisting ofSalmonella typhimurium, Salmonella javiana, Campylocater jejuin,Listeria monocytogenes, Escherichia coli 0157:H7, and mixtures thereof.12. The composition of claim 1, wherein the compound is present in anamount effective for reducing a population of a microorganism selectedfrom the group consisting of Staphylococcus aureus, Pseudomonasaeruginosa, methicillin-resistant Staphylococcus aureus, Bacillussubtilis, Bacillus cereus, Clostridium sporogenes, Clostridiumbotulinum, Clostridium difficile, Clostridium sporogenes and mixturesthereof.
 13. The composition of claim 1, wherein the oxidizing agentcomprises hydrogen peroxide, an organic peracid, an organic peroxide, orcombinations thereof.
 14. The composition of claim 1, wherein thecarboxylic acid is comprised of at least one C₁ to C₂₂ carboxylic acidin combination with at least one C₁ to C₂₂ peroxycarboxylic acid. 15.The composition of claim 14, wherein the peroxycarboxylic acid comprisesat least one C2 to C11 peroxycarboxylic acid.
 16. The composition ofclaim 15, wherein the peroxycarboxylic acid comprises peroxyoctanoicacid, peroxynonanoic acid, peroxydecanoic acid, or combinations thereof.17. The composition of claim 16, wherein the peroxyoctanoic acid ispresent at about 0.1 wt % to about 10 wt %.
 18. The composition of claim15, wherein the peroxycarboxylic acid comprises peroxyacids of acetic,glycolic, butyric, hexanoic, heptanoic, salicylic, malic, mandelic,malonic, succinic, glutaric, adipic, and citric acids, and mixturesthereof.
 19. The composition of claim 18, wherein the peroxycarboxylicacid is present at about 0.1 wt % to about 10 wt %.
 20. The compositionof claim 1, wherein the stabilizing agent is selected from the groupconsisting of organic amino polyphosphonic acid complexing agents,organic hydroxyl polyphosphonic acid complexing agents, and mixturesthereof.
 21. The composition of claim 1, wherein the stabilizing agentis selected from the group consisting of carboxylic acids,hydroxycarboxylic acids, aminocarboxylic acids, heterocyclic carboxylicacids and mixtures thereof.
 22. The composition of claim 1, wherein thecomposition is substantially phosphorous free.
 23. The composition ofclaim 1, wherein the composition comprises: (a) about 0.05 wt % to about50 wt % of a compound according to Formula I; (b) about 0.1 wt % toabout 75 wt % of the oxidizing agent; (c) about 0.1 wt % to about 40 wt% of the C₁-C₂₂ carboxylic acid in combination with one C₁ to C₂₂peroxycarboxylic acid; (d) about 0.50 wt % to about 70 wt % of thesurfactant; (e) about 0.0 wt % to about 5 wt % of an acid; and (f) about0.0 to about 10 wt % of a viscosity reducer.
 24. The composition ofclaim 2 wherein the viscosity reducer is comprised of propylene glycol.25. The composition of claim 1 wherein the surfactant is comprised of anonionic surfactant, anionic surfactant, amine oxide surfactant, ormixtures thereof.
 26. The composition of claim 1 wherein the stabilizingagent is comprised of dipicolinic acid.
 27. The composition of claim 23wherein the acid is comprised of sulfuric acid, methane sulfonic acid,ethane sulfonic acid, propane sulfonic acid, butane sulfonic acid,xylene sulfonic acid, benzene sulfonic acid, linear alkyl benzenesulphonic acid, cumene sulfonic acid, xylene sulfonic acid, formic acid,acetic acid, and combinations thereof.
 28. The composition of claim 25wherein the anionic surfactant is comprised of linear alkyl benzenesulphonate or linear alkyl benzene sulfonic acid, or mixtures thereof.